메뉴 건너뛰기




Volumn 26, Issue 7, 2007, Pages 369-394

Highly efficient α-sialylation by virtue of fixed dipole effects of N-phthalyl group: Application to continuous flow synthesis of α(2-3)-and α(2-6)-Neu5Ac-Gal motifs by microreactor

Author keywords

Sialylation; Fixed dipole effects; Microreactor; N Phthalyl group; Oligosaccharides

Indexed keywords


EID: 35948960286     PISSN: 07328303     EISSN: 15322327     Source Type: Journal    
DOI: 10.1080/07328300701634796     Document Type: Article
Times cited : (55)

References (75)
  • 1
    • 0027318961 scopus 로고
    • Biological roles of oligosaccharides: All of the theories are correct
    • (a) Varki, A. Biological roles of oligosaccharides: All of the theories are correct. Glycobiology 1993, 3, 97-130;
    • (1993) Glycobiology , vol.3 , pp. 97-130
    • Varki, A.1
  • 2
    • 0003631621 scopus 로고
    • Rosenberg, A. Ed, Plenum Press: New York, London
    • (b) Rosenberg, A. Ed.; Biology of Sialic Acids; Plenum Press: New York, London, 1995;
    • (1995) Biology of Sialic Acids
  • 3
    • 84956519119 scopus 로고    scopus 로고
    • Biochemistry of sialic acid diversity
    • Ernst, B, Hart, G.W, and Sinaÿ, P, Eds, Wiley-VCH: Weinheim
    • (c) Schauer, R. Biochemistry of sialic acid diversity. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G.W., and Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 3, 227-243;
    • (2000) Carbohydrates in Chemistry and Biology , vol.3 , pp. 227-243
    • Schauer, R.1
  • 4
    • 0035562545 scopus 로고    scopus 로고
    • Sialic acid and glycobiology: A chemical approach
    • (d) Ando, T.; Ando, H.; Kiso, M. Sialic acid and glycobiology: A chemical approach. Trend. Glycosci. Glycotech. 2001, 13, 573-586;
    • (2001) Trend. Glycosci. Glycotech , vol.13 , pp. 573-586
    • Ando, T.1    Ando, H.2    Kiso, M.3
  • 5
    • 0036816141 scopus 로고    scopus 로고
    • Lubricating cell signaling pathways with gangliosides
    • (e) Allende, M.L.; Proia, R.L. Lubricating cell signaling pathways with gangliosides. Curr. Opin. Struct. Biol. 2002, 12, 587-592;
    • (2002) Curr. Opin. Struct. Biol , vol.12 , pp. 587-592
    • Allende, M.L.1    Proia, R.L.2
  • 6
    • 0036815746 scopus 로고    scopus 로고
    • Sialic-acid-binding immunoglobulin-like lectins in cell-cell interactions and signaling
    • (f) Crocker, P.R. Siglecs: Sialic-acid-binding immunoglobulin-like lectins in cell-cell interactions and signaling. Curr. Opin. Struct. Biol. 2002, 12, 609-615;
    • (2002) Curr. Opin. Struct. Biol , vol.12 , pp. 609-615
    • Crocker, P.R.S.1
  • 7
    • 0036816134 scopus 로고    scopus 로고
    • Structure and function of water channels
    • (g) Kannagi, R. Structure and function of water channels. Curr. Opin. Struct. Biol. 2002, 12, 599-608.
    • (2002) Curr. Opin. Struct. Biol , vol.12 , pp. 599-608
    • Kannagi, R.1
  • 8
    • 0024301085 scopus 로고
    • A facile regio- and stereo-selective synthesis of α-glycosides of N-acetylneuraminic acid
    • (a) Murase, T.; Ishida, H.; Kiso, M.; Hasegawa, A. A facile regio- and stereo-selective synthesis of α-glycosides of N-acetylneuraminic acid. Carbohydr. Res. 1988, 184, C1-C4;
    • (1988) Carbohydr. Res , vol.184
    • Murase, T.1    Ishida, H.2    Kiso, M.3    Hasegawa, A.4
  • 10
    • 0001728392 scopus 로고
    • Studies on the thioglycosides of N-acetylneuraminic acid. Part 5. Glycosylation using methyl thioglycosides of N-acetylneuraminic acid and dimethyl(methylthio) sulfonium triflate
    • (c) Kanie, O.; Kiso, M.; Hasegawa, A. Studies on the thioglycosides of N-acetylneuraminic acid. Part 5. Glycosylation using methyl thioglycosides of N-acetylneuraminic acid and dimethyl(methylthio) sulfonium triflate. J. Carbohydr. Chem. 1988, 7, 501-506;
    • (1988) J. Carbohydr. Chem , vol.7 , pp. 501-506
    • Kanie, O.1    Kiso, M.2    Hasegawa, A.3
  • 11
    • 0001199265 scopus 로고
    • Benzeneselenenyl triflate as a promoter of thioglycosides: A new method for O-glycosylation using thioglycosides
    • (d) Ito, Y.; Ogawa, T. Benzeneselenenyl triflate as a promoter of thioglycosides: A new method for O-glycosylation using thioglycosides. Tetrahedron Lett. 1988, 29, 1061-1064;
    • (1988) Tetrahedron Lett , vol.29 , pp. 1061-1064
    • Ito, Y.1    Ogawa, T.2
  • 12
    • 44949268152 scopus 로고
    • A novel stereoselective synthesis of N-acetyl-α-neuraminosyl-galactose di-saccharide derivatives, using anomeric S-glycosyl xanthates
    • (e) Marra, A.; Sina, P. A novel stereoselective synthesis of N-acetyl-α-neuraminosyl-galactose di-saccharide derivatives, using anomeric S-glycosyl xanthates. Carbohydr. Res. 1990, 195, 303-308;
    • (1990) Carbohydr. Res , vol.195 , pp. 303-308
    • Marra, A.1    Sina, P.2
  • 13
    • 0025708060 scopus 로고
    • Benzeneselenenyl triflate as an activator of thioglycosides for glycosylation reactions
    • (f) Ito, Y.; Ogawa, T. Benzeneselenenyl triflate as an activator of thioglycosides for glycosylation reactions. Carbohydr. Res. 1990, 202, 165-175;
    • (1990) Carbohydr. Res , vol.202 , pp. 165-175
    • Ito, Y.1    Ogawa, T.2
  • 14
    • 0026327789 scopus 로고
    • α-Selectivity and glycal formation are temperature dependent in glycosylation with sialic acid. Synthesis of a Neu5Acα(2-6)Gal thioglycoside building
    • (g) Birberg, W.; Lonn, H. α-Selectivity and glycal formation are temperature dependent in glycosylation with sialic acid. Synthesis of a Neu5Acα(2-6)Gal thioglycoside building. Tetrahedron Lett. 1991, 32, 7453-7456;
    • (1991) Tetrahedron Lett , vol.32 , pp. 7453-7456
    • Birberg, W.1    Lonn, H.2
  • 15
    • 0026173653 scopus 로고
    • A facile, large-scale preparation of the methyl 2-thioglycoside of N-acetylneuraminic acid, and its usefulness for the α-stereoselective synthesis of sialoglycosides
    • (h) Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. A facile, large-scale preparation of the methyl 2-thioglycoside of N-acetylneuraminic acid, and its usefulness for the α-stereoselective synthesis of sialoglycosides. Carbohydr. Res. 1991, 212, 277-281;
    • (1991) Carbohydr. Res , vol.212 , pp. 277-281
    • Hasegawa, A.1    Ohki, H.2    Nagahama, T.3    Ishida, H.4    Kiso, M.5
  • 16
    • 33749479027 scopus 로고
    • Synthetic studies on sialoglycoconjugates. 25. Reactivity of glycosyl promoters in α-glycosylation of N-acetylneuraminic acid with the primary and secondary hydroxyl groups in the suitably protected galactose and lactose derivatives
    • (i) Hasegawa, A.; Nagahama, T.; Ohki, H.; Hotta, K.; Ishida, H.; Kiso, M. Synthetic studies on sialoglycoconjugates. 25. Reactivity of glycosyl promoters in α-glycosylation of N-acetylneuraminic acid with the primary and secondary hydroxyl groups in the suitably protected galactose and lactose derivatives. J. Carbohydr. Chem. 1991, 10, 493-498;
    • (1991) J. Carbohydr. Chem , vol.10 , pp. 493-498
    • Hasegawa, A.1    Nagahama, T.2    Ohki, H.3    Hotta, K.4    Ishida, H.5    Kiso, M.6
  • 17
    • 0000576352 scopus 로고
    • β-Sialyl phosphite and phosphoramidite: Synthesis and application to the chemoenzymic synthesis of CMP-sialic acid and sialyl oligosaccharides
    • (j) Kondo, H.; Ichikawa, Y.; Wong, C.-H. β-Sialyl phosphite and phosphoramidite: synthesis and application to the chemoenzymic synthesis of CMP-sialic acid and sialyl oligosaccharides. J. Am. Chem. Soc. 1992, 114, 8748-8750;
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 8748-8750
    • Kondo, H.1    Ichikawa, Y.2    Wong, C.-H.3
  • 18
    • 0026675928 scopus 로고
    • Active" and "latent" thioglycosyl donors in oligosaccharide synthesis. Application to the synthesis of α-sialosides
    • (k) Roy, R.; Andersson, F.O.; Letellier, M. "Active" and "latent" thioglycosyl donors in oligosaccharide synthesis. Application to the synthesis of α-sialosides. Tetrahedron Lett. 1992, 33, 6053-6056;
    • (1992) Tetrahedron Lett , vol.33 , pp. 6053-6056
    • Roy, R.1    Andersson, F.O.2    Letellier, M.3
  • 19
    • 0026658833 scopus 로고
    • Efficient sialylation with phosphite as leaving group
    • (l) Martin, T.J.; Schmidt, R.R. Efficient sialylation with phosphite as leaving group. Tetrahedron Lett. 1992, 33, 6123-6126;
    • (1992) Tetrahedron Lett , vol.33 , pp. 6123-6126
    • Martin, T.J.1    Schmidt, R.R.2
  • 20
    • 0000331272 scopus 로고    scopus 로고
    • Martichonok, V.; Whitesides, G.M. Stereoselective α-sialylation with sialyl xanthate and phenylsulfenyl triflate as a promotor. J. Org. Chem. 1996, 61, 1702-1706;
    • (m) Martichonok, V.; Whitesides, G.M. Stereoselective α-sialylation with sialyl xanthate and phenylsulfenyl triflate as a promotor. J. Org. Chem. 1996, 61, 1702-1706;
  • 21
    • 0037436444 scopus 로고    scopus 로고
    • First total synthesis of α-(2 → 3)/α-(2 → 6)-disialyl lactotetraosyl ceramide and disialyl Lewis: A ganglioside as cancer-associated carbohydrate antigens
    • (n) Ando, T.; Ishida, H.; Kiso, M. First total synthesis of α-(2 → 3)/α-(2 → 6)-disialyl lactotetraosyl ceramide and disialyl Lewis: a ganglioside as cancer-associated carbohydrate antigens. Carbohydr. Res. 2003, 338, 503-514;
    • (2003) Carbohydr. Res , vol.338 , pp. 503-514
    • Ando, T.1    Ishida, H.2    Kiso, M.3
  • 22
    • 0034511734 scopus 로고    scopus 로고
    • Recent advances in O-sialylation
    • (o) Boons, B.J.; Demchenko, A.V. Recent advances in O-sialylation. Chem. Rev. 2000, 100, 4539-4566;
    • (2000) Chem. Rev , vol.100 , pp. 4539-4566
    • Boons, B.J.1    Demchenko, A.V.2
  • 23
    • 0035800385 scopus 로고    scopus 로고
    • The thioglycoside and glycosyl phosphite of 5-azido sialic acid: Excellent donors for the α-glycosylation of primary hydroxy groups
    • (p) Yu, C.-S.; Niikura, K.; Lin, C.-C.; Wong, C.-H. The thioglycoside and glycosyl phosphite of 5-azido sialic acid: excellent donors for the α-glycosylation of primary hydroxy groups. Angew. Chem. Int. Ed. 2001, 40, 2900-2903;
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 2900-2903
    • Yu, C.-S.1    Niikura, K.2    Lin, C.-C.3    Wong, C.-H.4
  • 24
    • 0035906841 scopus 로고    scopus 로고
    • Synthesis of ganglioside GD3 and its comparison with bovine GD3 with regard to oligodendrocyte apoptosis mitochondrial damage
    • (q) Castro-Palomino, J.C.; Simon, B.; Speer, O.; Leist, M.; Schmidt, R.R. Synthesis of ganglioside GD3 and its comparison with bovine GD3 with regard to oligodendrocyte apoptosis mitochondrial damage. Chem. Eur. J. 2001, 7, 2178-2184;
    • (2001) Chem. Eur. J , vol.7 , pp. 2178-2184
    • Castro-Palomino, J.C.1    Simon, B.2    Speer, O.3    Leist, M.4    Schmidt, R.R.5
  • 25
    • 0035838878 scopus 로고    scopus 로고
    • A stereoselective approach for the synthesis of α-sialosides
    • (r) De MeO, C.; Demchenko, A.V.; Boons, G.J. A stereoselective approach for the synthesis of α-sialosides. J. Org. Chem. 2001, 66, 5490-5497;
    • (2001) J. Org. Chem , vol.66 , pp. 5490-5497
    • De MeO, C.1    Demchenko, A.V.2    Boons, G.J.3
  • 26
    • 0035910546 scopus 로고    scopus 로고
    • The 2-naphthylmethyl (NAP) group in carbohydrate synthesis: First total synthesis of the GlyCAM-1 oligosaccharide structures
    • (s) Xia, J.; Alderfer, J.L.; Piskorz, C.F.; Matta, K.L. The 2-naphthylmethyl (NAP) group in carbohydrate synthesis: First total synthesis of the GlyCAM-1 oligosaccharide structures. Chem. Eur. J. 2001, 7, 356-367;
    • (2001) Chem. Eur. J , vol.7 , pp. 356-367
    • Xia, J.1    Alderfer, J.L.2    Piskorz, C.F.3    Matta, K.L.4
  • 27
    • 0038246313 scopus 로고    scopus 로고
    • Recent developments in technology for glycosylation with sialic acid
    • (t) Halcomb, R.L.; Chappell, M.D. Recent developments in technology for glycosylation with sialic acid. J. Carbohydr. Chem. 2002, 21, 723-768;
    • (2002) J. Carbohydr. Chem , vol.21 , pp. 723-768
    • Halcomb, R.L.1    Chappell, M.D.2
  • 28
    • 0037154776 scopus 로고    scopus 로고
    • Synthesis of a sialic acid dimer derivative, 2′ αO-benzyl Neu5Ac-α-(2 → 5)Neu5Gc
    • (u) Ren, C.-T.; Chen, C.-S.; Wu, S.-H. Synthesis of a sialic acid dimer derivative, 2′ αO-benzyl Neu5Ac-α-(2 → 5)Neu5Gc. J. Org. Chem. 2002, 67, 1376-1379;
    • (2002) J. Org. Chem , vol.67 , pp. 1376-1379
    • Ren, C.-T.1    Chen, C.-S.2    Wu, S.-H.3
  • 29
    • 0141519625 scopus 로고    scopus 로고
    • Dehydrative sialylation with C2-hemiketal sialyl donors
    • (v) Haberman, J.M.; Gin, D.Y. Dehydrative sialylation with C2-hemiketal sialyl donors. Org. Lett. 2003, 5, 2539-2541.
    • (2003) Org. Lett , vol.5 , pp. 2539-2541
    • Haberman, J.M.1    Gin, D.Y.2
  • 30
    • 0024287221 scopus 로고
    • A total synthesis of hematoside, α-NeuGc-(2 → 3)-β-Gal-(1 → 4)-β-Glc-(1 → 1)-Cer
    • Representative examples of N-glycolyl derivatives, see: a
    • Representative examples of N-glycolyl derivatives, see: (a) Numata, M.; Sugimoto, M.; Shibayama, S.; Ogawa, T. A total synthesis of hematoside, α-NeuGc-(2 → 3)-β-Gal-(1 → 4)-β-Glc-(1 → 1)-Cer. Carbohydr. Res. 1988, 174, 73-85;
    • (1988) Carbohydr. Res , vol.174 , pp. 73-85
    • Numata, M.1    Sugimoto, M.2    Shibayama, S.3    Ogawa, T.4
  • 33
    • 0029316055 scopus 로고
    • Synthetic studies on sialoglyco-conjugates. Part 67. Synthesis of a sialyl Lewis X ganglioside analog containing N-glycolyl in place of the N-acetyl group in the N-acetylneuramic acid residue
    • (d) Hasegawa, A.; Uchimura, A.; Ishida, H.; Kiso, M. Synthetic studies on sialoglyco-conjugates. Part 67. Synthesis of a sialyl Lewis X ganglioside analog containing N-glycolyl in place of the N-acetyl group in the N-acetylneuramic acid residue. Biosci. Biotech. Biochem. 1995, 59, 1091-1094;
    • (1995) Biosci. Biotech. Biochem , vol.59 , pp. 1091-1094
    • Hasegawa, A.1    Uchimura, A.2    Ishida, H.3    Kiso, M.4
  • 34
    • 0029918105 scopus 로고    scopus 로고
    • A facile preparation of the methyl 2-thioglycoside of N-glycolylneuraminic acid, an efficient donor of NeuGc
    • (e) Sugata, T.; Higuchi, R. A facile preparation of the methyl 2-thioglycoside of N-glycolylneuraminic acid, an efficient donor of NeuGc. Tetrahedron Lett. 1996, 37, 2613-2614;
    • (1996) Tetrahedron Lett , vol.37 , pp. 2613-2614
    • Sugata, T.1    Higuchi, R.2
  • 35
    • 0035961440 scopus 로고    scopus 로고
    • Synthesis of Neu5Ac- and Neu5Gc-a-(2 → 6′)- lactosamine 3-aminopropyl glycosides
    • (f) Scherman, A.A.; Yudina, O.N.; Shashkov, A.S.; Menshov, V.M.; Nifant'ev, N.E. Synthesis of Neu5Ac- and Neu5Gc-a-(2 → 6′)- lactosamine 3-aminopropyl glycosides. Carbohydr. Res. 2001, 330, 445-458;
    • (2001) Carbohydr. Res , vol.330 , pp. 445-458
    • Scherman, A.A.1    Yudina, O.N.2    Shashkov, A.S.3    Menshov, V.M.4    Nifant'ev, N.E.5
  • 36
    • 0026848886 scopus 로고
    • Total synthesis of the modified ganglioside de-N-acetyl-GM3 and some analogs
    • (g) Fujita, S.; Numata, M.; Sugimoto, M.; Tomita, K.; Ogawa, T. Total synthesis of the modified ganglioside de-N-acetyl-GM3 and some analogs. Carbohydr. Res. 1992, 228, 347-370;
    • (1992) Carbohydr. Res , vol.228 , pp. 347-370
    • Fujita, S.1    Numata, M.2    Sugimoto, M.3    Tomita, K.4    Ogawa, T.5
  • 37
    • 0033583457 scopus 로고    scopus 로고
    • The first total synthesis of 6-sulfo-de-N-acetylsialyl LewisX ganglioside: A superior ligand for human L-selectin
    • (h) Komba, S.; Galustian, C.; Ishida, H.; Feizi, T.; Kannagi, R.; Kiso, M. The first total synthesis of 6-sulfo-de-N-acetylsialyl LewisX ganglioside: A superior ligand for human L-selectin. Angew. Chem. Int. Ed. 1999, 38, 1131-1133;
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 1131-1133
    • Komba, S.1    Galustian, C.2    Ishida, H.3    Feizi, T.4    Kannagi, R.5    Kiso, M.6
  • 38
    • 0035536166 scopus 로고    scopus 로고
    • Example for 1,5-lactam derivatives: (i) Otsubo, N.; Yamaguchi, M.; Ishida, H.; Kiso, M. Synthetic studies of sialo-glyconjugates. Part 120. The first, efficient synthesis of novel SLex neoglycolipids containing N-deacetylated and lactamized sialic acid: Key ligand structures for selectin binding. J. Carbohydr. Chem. 2001, 20, 329-334.
    • Example for 1,5-lactam derivatives: (i) Otsubo, N.; Yamaguchi, M.; Ishida, H.; Kiso, M. Synthetic studies of sialo-glyconjugates. Part 120. The first, efficient synthesis of novel SLex neoglycolipids containing N-deacetylated and lactamized sialic acid: Key ligand structures for selectin binding. J. Carbohydr. Chem. 2001, 20, 329-334.
  • 39
    • 0028186224 scopus 로고
    • Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method
    • (a) Schmidt, R.R.; Kinzy, W. Anomeric-oxygen activation for glycoside synthesis: The trichloroacetimidate method. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123;
    • (1994) Adv. Carbohydr. Chem. Biochem , vol.50 , pp. 21-123
    • Schmidt, R.R.1    Kinzy, W.2
  • 41
    • 0024992421 scopus 로고
    • Glycosidation of sialic acid
    • (a) Okamoto, K.; Goto, T. Glycosidation of sialic acid. Tetrahedron. 1990, 46, 5835-5857;
    • (1990) Tetrahedron , vol.46 , pp. 5835-5857
    • Okamoto, K.1    Goto, T.2
  • 42
    • 0025745022 scopus 로고
    • The synthesis and glycosidation on N-acetylneuraminic acid
    • (b) DeNinno, M.P. The synthesis and glycosidation on N-acetylneuraminic acid. Synthesis 1991, 583-593;
    • (1991) Synthesis , pp. 583-593
    • DeNinno, M.P.1
  • 43
    • 0034511734 scopus 로고    scopus 로고
    • Recent advances in O-sialylation
    • (c) Boons, G.-J.; Demchenko, A.V. Recent advances in O-sialylation. Chem. Rev. 2000, 100, 4539-4565.
    • (2000) Chem. Rev , vol.100 , pp. 4539-4565
    • Boons, G.-J.1    Demchenko, A.V.2
  • 44
    • 0242712852 scopus 로고    scopus 로고
    • Efficient sialylation with phenyltrifluoroacetimidates as leaving groups
    • Cai, S.; Yu, B. Efficient sialylation with phenyltrifluoroacetimidates as leaving groups. Org. Lett. 2003, 5, 3827-3830.
    • (2003) Org. Lett , vol.5 , pp. 3827-3830
    • Cai, S.1    Yu, B.2
  • 45
    • 0042159799 scopus 로고    scopus 로고
    • Extending the possibility of an N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis
    • Ando, H.; Koike, Y.; Ishida, H.; Kiso, M. Extending the possibility of an N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis. Tetrahedron Lett. 2003, 44, 6883-6886.
    • (2003) Tetrahedron Lett , vol.44 , pp. 6883-6886
    • Ando, H.1    Koike, Y.2    Ishida, H.3    Kiso, M.4
  • 46
    • 1642338668 scopus 로고    scopus 로고
    • Synthetic study of α(2,8) oligosaccharide using N-Troc sialyl N-phenyltrifluoroimidate
    • Adachi, M.; Tanaka, H.; Takahashi, T. Synthetic study of α(2,8) oligosaccharide using N-Troc sialyl N-phenyltrifluoroimidate. Synlett 2004, 609-614.
    • (2004) Synlett , pp. 609-614
    • Adachi, M.1    Tanaka, H.2    Takahashi, T.3
  • 47
    • 27444438620 scopus 로고    scopus 로고
    • 1,5-Lactamized sialyl acceptors for various disaccharide syntheses: Novel method for the synthesis of glycan portions of Hp-s6 and HLG-2 gangliosides
    • (a) Ando, H.; Koike, Y.; Koizumi, S.; Ishida, H.; Kiso, M. 1,5-Lactamized sialyl acceptors for various disaccharide syntheses: Novel method for the synthesis of glycan portions of Hp-s6 and HLG-2 gangliosides. Angew. Chem. Int. Ed. 2005, 44, 6759-6763;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 6759-6763
    • Ando, H.1    Koike, Y.2    Koizumi, S.3    Ishida, H.4    Kiso, M.5
  • 48
    • 33744918059 scopus 로고    scopus 로고
    • Stereoselective synthesis of oligo-α-(2,8)-sialic acids
    • (b) Tanaka, H.; Nishiura, Y.; Takahashi, T. Stereoselective synthesis of oligo-α-(2,8)-sialic acids. J. Am. Chem. Soc. 2006, 128, 7124-7125.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 7124-7125
    • Tanaka, H.1    Nishiura, Y.2    Takahashi, T.3
  • 49
    • 28844435773 scopus 로고    scopus 로고
    • Highly efficient sialylation towards α(2-3) and α(2-6)-Neu5Ac-Gal synthesis: Significant "fixed dipole effect" of N-phthalyl group on α-selectivity
    • Tanaka, K.; Goi, T.; Fukase, K. Highly efficient sialylation towards α(2-3) and α(2-6)-Neu5Ac-Gal synthesis: Significant "fixed dipole effect" of N-phthalyl group on α-selectivity. Synlett 2005, 2958-2962.
    • (2005) Synlett , pp. 2958-2962
    • Tanaka, K.1    Goi, T.2    Fukase, K.3
  • 50
    • 0028004561 scopus 로고
    • Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors
    • Cao, S.; Meunier, S.J.; Andersson, F.O.; Letellier, M.; Roy, R. Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors. Tetrahedron Asymm. 1994, 5, 2303-2312.
    • (1994) Tetrahedron Asymm , vol.5 , pp. 2303-2312
    • Cao, S.1    Meunier, S.J.2    Andersson, F.O.3    Letellier, M.4    Roy, R.5
  • 51
    • 0001485197 scopus 로고
    • 1H-NMR studies at N-acetyl-D-neuraminic acid ketosides for the determination of the anomeric configuration II
    • 1H-NMR studies at N-acetyl-D-neuraminic acid ketosides for the determination of the anomeric configuration II. Tetrahedron Lett. 1979, 20, 4637-4640;
    • (1979) Tetrahedron Lett , vol.20 , pp. 4637-4640
    • Dabrowski, U.1    Friebolin, H.2    Brossmer, R.3    Supp, M.4
  • 52
    • 84985611066 scopus 로고
    • Synthesis of trisaccharide moieties from N-acetylneuraminic acid and N-acetyllactosamine
    • (b) Paulsen, H.; Tietz, H. Synthesis of trisaccharide moieties from N-acetylneuraminic acid and N-acetyllactosamine. Angew. Chem. Int. Ed. 1982, 21, 927-928.
    • (1982) Angew. Chem. Int. Ed , vol.21 , pp. 927-928
    • Paulsen, H.1    Tietz, H.2
  • 53
    • 0001728392 scopus 로고
    • Studies on the thioglycosides of N-acetylneuraminic acid. Part 5. Glycosylation using methyl thioglycosides of N-acetylneuraminic acid and dimethyl(methylthio) sulfonium triflate
    • (a) Kanie, O.; Kiso, M.; Hasegawa, A. Studies on the thioglycosides of N-acetylneuraminic acid. Part 5. Glycosylation using methyl thioglycosides of N-acetylneuraminic acid and dimethyl(methylthio) sulfonium triflate. J. Carbohydr. Chem. 1988, 7, 501-506;
    • (1988) J. Carbohydr. Chem , vol.7 , pp. 501-506
    • Kanie, O.1    Kiso, M.2    Hasegawa, A.3
  • 54
    • 0001763001 scopus 로고
    • Stereoselective glycosidations of uronic acids
    • (b) Schmidt, R.R.; Rucker, E. Stereoselective glycosidations of uronic acids. Tetrahedron Lett. 1980, 21, 1421-1424;
    • (1980) Tetrahedron Lett , vol.21 , pp. 1421-1424
    • Schmidt, R.R.1    Rucker, E.2
  • 55
    • 37049089952 scopus 로고
    • Generation of α-D- glucopyranosylacetonitrilium ions. Concerning the reverse anomeric effect
    • (c) Ratcliffe, A.J.; Fraser-Reid, B. Generation of α-D- glucopyranosylacetonitrilium ions. Concerning the reverse anomeric effect. J. Chem. Soc. Perkin Trans. 1 1990, 747-750.
    • (1990) J. Chem. Soc. Perkin Trans. 1 , pp. 747-750
    • Ratcliffe, A.J.1    Fraser-Reid, B.2
  • 56
    • 0003679611 scopus 로고    scopus 로고
    • Representative reviews, see: (a) Ehrfeld, W. Ed, Springer: Berlin
    • Representative reviews, see: (a) Ehrfeld, W. Ed.; Microreaction Technology; Springer: Berlin, 1998.
    • (1998) Microreaction Technology
  • 60
    • 23144442783 scopus 로고    scopus 로고
    • Selective organic reactions using microreactors
    • (e) Yoshida, J.-I.; Suga, S.; Nagaki, A. Selective organic reactions using microreactors. J. Synth. Org. Chem. 2005, 63, 511-522.
    • (2005) J. Synth. Org. Chem , vol.63 , pp. 511-522
    • Yoshida, J.-I.1    Suga, S.2    Nagaki, A.3
  • 61
    • 9944240339 scopus 로고    scopus 로고
    • Chemical microprocess technology-from laboratory-scale to production
    • Recent applications, see: a
    • Recent applications, see: (a) Pennemann, H.; Hessel, V.; Loewe, H. Chemical microprocess technology-from laboratory-scale to production. Chem. Engineer. Sci. 2004, 59, 4789-4794.
    • (2004) Chem. Engineer. Sci , vol.59 , pp. 4789-4794
    • Pennemann, H.1    Hessel, V.2    Loewe, H.3
  • 63
    • 23944512793 scopus 로고    scopus 로고
    • Control of extremely fast competitive consecutive reactions using micromixing. Selective Friedel-Crafts aminoalkylation
    • (c) Nagaki, A.; Togai, M.; Suga, S.; Aoki, N.; Mae, K.; Yoshida, J.-I. Control of extremely fast competitive consecutive reactions using micromixing. Selective Friedel-Crafts aminoalkylation. J. Am. Chem. Soc. 2005, 127, 11666-11675;
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 11666-11675
    • Nagaki, A.1    Togai, M.2    Suga, S.3    Aoki, N.4    Mae, K.5    Yoshida, J.-I.6
  • 64
    • 33846404910 scopus 로고    scopus 로고
    • Efficient procedure for reductive opening of sugar 4,6-O-benzylidene acetals by a microfluidic system
    • (d) Tanaka, K.; Fukase, K. Efficient procedure for reductive opening of sugar 4,6-O-benzylidene acetals by a microfluidic system. Synlett, 2007, 164-166;
    • (2007) Synlett , pp. 164-166
    • Tanaka, K.1    Fukase, K.2
  • 65
    • 33846583611 scopus 로고    scopus 로고
    • Large-scale synthesis of immunoactivating natural product, pristane, by continuous microfluidic dehydration as key step
    • (e) Tanaka, K.; Motomatsu, S.; Koyama, K.; Tanaka, S.-I.; Fukase, K. Large-scale synthesis of immunoactivating natural product, pristane, by continuous microfluidic dehydration as key step. Org. Lett. 2007, 9, 299-302.
    • (2007) Org. Lett , vol.9 , pp. 299-302
    • Tanaka, K.1    Motomatsu, S.2    Koyama, K.3    Tanaka, S.-I.4    Fukase, K.5
  • 67
    • 25444519769 scopus 로고    scopus 로고
    • Oligosaccharide synthesis by using affinity separation based on molecular recognition between podand ether and ammonium ion
    • (b) Fukase, K.; Takashina, M.; Hori, Y.; Tanaka, D.; Tanaka, K.; Kusumoto, S. Oligosaccharide synthesis by using affinity separation based on molecular recognition between podand ether and ammonium ion. Synlett 2005, 2342-2346.
    • (2005) Synlett , pp. 2342-2346
    • Fukase, K.1    Takashina, M.2    Hori, Y.3    Tanaka, D.4    Tanaka, K.5    Kusumoto, S.6
  • 69
    • 0037571112 scopus 로고    scopus 로고
    • Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94
    • (a) Halgren, T.A. Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519;
    • (1996) J. Comput. Chem , vol.17 , pp. 490-519
    • Halgren, T.A.1
  • 70
    • 0011134241 scopus 로고    scopus 로고
    • Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions
    • (b) Halgren, T.A. Merck molecular force field. II. MMFF94 van der Waals and electrostatic parameters for intermolecular interactions. J. Comput. Chem. 1996, 17, 520-552;
    • (1996) J. Comput. Chem , vol.17 , pp. 520-552
    • Halgren, T.A.1
  • 71
    • 0011143599 scopus 로고    scopus 로고
    • Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94
    • (c) Halgren, T.A. Merck molecular force field. III. Molecular geometries and vibrational frequencies for MMFF94. J. Comput. Chem. 1996, 17, 553-586;
    • (1996) J. Comput. Chem , vol.17 , pp. 553-586
    • Halgren, T.A.1
  • 72
    • 0001061464 scopus 로고    scopus 로고
    • Merck molecular force field. IV. conformational energies and geometries for MMFF94
    • (d) Halgren, T.A.; Nachbar, R.B. Merck molecular force field. IV. conformational energies and geometries for MMFF94. J. Comput. Chem. 1996, 17, 587-615;
    • (1996) J. Comput. Chem , vol.17 , pp. 587-615
    • Halgren, T.A.1    Nachbar, R.B.2
  • 73
    • 5244268272 scopus 로고    scopus 로고
    • Merck molecular force field. V. Extension of MMFF94 using experimental data, additional computational data, and empirical rules
    • (e) Halgren, T.A. Merck molecular force field. V. Extension of MMFF94 using experimental data, additional computational data, and empirical rules. J. Comput. Chem. 1996, 17, 616-641.
    • (1996) J. Comput. Chem , vol.17 , pp. 616-641
    • Halgren, T.A.1
  • 75
    • 35948946400 scopus 로고    scopus 로고
    • Frisch, M.J, Trucks, G.W, Schlegel, H.B, Scuseria, G.E, Robb, M.A, Cheeseman, J.R, Zakrzewski, V.G, Montgomery, J.A, Jr, Stratmann, R.E, Burant, J.C, Dapprich, S, Illam, J.M, Daniels, A.D, Kudin, K.N, Strain, M.C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G.A, Ayala, P.Y, Cui, Q, Morokuma, K, Malick, D.K, Rabuck, A.D, Raghavachari, K, Foresman, J.B, Cioslowski, J, Ortiz, J.V, Stefanov, B.B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R.L, Fox, D.J, Keith, T, Al-Laham, M.A, Peng, C.Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P.M.W, Johnson, B.G, Chen, W, Wong, M.W, Andres, J.L, Head-Gordon, M, Replogle, E.S, Pople, J.A. Gaussian 03; Gaussian, Inc, Pittsburgh, PA, USA, 2003
    • Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A., Jr.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Illam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M.W.; Johnson, B.G.; Chen, W.; Wong, M.W.; Andres, J.L.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. Gaussian 03; Gaussian, Inc.: Pittsburgh, PA, USA, 2003, http://www.gaussian.com/.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.