메뉴 건너뛰기




Volumn 1, Issue 3, 2006, Pages 281-286

The approach to the synthesis of novel amino-C-glycosides

Author keywords

1,3 dipolar cycloaddition; C glycoside; Exo glycal; Ketosyl spiro isoxazolidine

Indexed keywords


EID: 33749342433     PISSN: 16733495     EISSN: 16733614     Source Type: Journal    
DOI: 10.1007/s11458-006-0040-y     Document Type: Article
Times cited : (5)

References (40)
  • 2
  • 3
    • 0003713167 scopus 로고    scopus 로고
    • Blackie Academic and Professional, London
    • Boons G.J. Carbohydrate Chemistry, Blackie Academic and Professional, London, 1998, pp. 399-408
    • (1998) Carbohydrate Chemistry , pp. 399-408
    • Boons, G.J.1
  • 4
    • 0034746037 scopus 로고    scopus 로고
    • Carbanionic reactivity of the anomeric center in carbohydrates
    • Somsak L., Carbanionic Reactivity of the Anomeric Center in Carbohydrates, Chem. Rev., 2001, 101: 81-135
    • (2001) Chem. Rev. , vol.101 , pp. 81-135
    • Somsak, L.1
  • 5
    • 0032552046 scopus 로고    scopus 로고
    • Recent advances in stereoselective C-glycoside synthesis
    • Du Y. and Linhardt R.J., Recent advances in stereoselective C-glycoside synthesis, Tetrahedron, 1998, 54: 9913-9959
    • (1998) Tetrahedron , vol.54 , pp. 9913-9959
    • Du, Y.1    Linhardt, R.J.2
  • 6
    • 0034507032 scopus 로고    scopus 로고
    • Methods for anomeric carbon-linked and fused sugar amino acid synthesis: The gateway to artificial glycopeptides
    • Dondoni A. and Marra A, Methods for Anomeric Carbon-Linked and Fused Sugar Amino Acid Synthesis: The Gateway to Artificial Glycopeptides, Chem. Rev., 2000, 100: 4395-4421
    • (2000) Chem. Rev. , vol.100 , pp. 4395-4421
    • Dondoni, A.1    Marra, A.2
  • 7
    • 0035713714 scopus 로고    scopus 로고
    • Synthesis of C- saccharides and higher congeners
    • Liu L., McKee M.M. and Postema H.D., Synthesis of C- Saccharides and Higher Congeners, Curr. Org. Chem., 2001, 5: 1133-1167
    • (2001) Curr. Org. Chem. , vol.5 , pp. 1133-1167
    • Liu, L.1    McKee, M.M.2    Postema, H.D.3
  • 8
    • 0037259151 scopus 로고    scopus 로고
    • Carbohydrate derivatives containing the carbon-lithium and carbon-tin bonds
    • Jarosz S. and Zamojski A., Carbohydrate Derivatives Containing the Carbon-Lithium and Carbon-Tin Bonds, Curr. Org. Chem., 2003, 7: 13-33
    • (2003) Curr. Org. Chem. , vol.7 , pp. 13-33
    • Jarosz, S.1    Zamojski, A.2
  • 9
    • 0037371046 scopus 로고    scopus 로고
    • 1,3-dipolar cycloadditions in the synthesis of carbohydrate mimics. Part 1: Nitrile oxides and nitronates
    • a) Gallos J.K. and Koumbis A.E., 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 1: Nitrile Oxides and Nitronates, Curr. Org. Chem., 2003, 7: 397-426
    • (2003) Curr. Org. Chem. , vol.7 , pp. 397-426
    • Gallos, J.K.1    Koumbis, A.E.2
  • 10
    • 0037377598 scopus 로고    scopus 로고
    • 1,3-dipolar cycloadditions in the synthesis of carbohydrate mimics. Part 2: Nitrones and oximes
    • b) Koumbis A.E. and Gallos J.K., 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 2: Nitrones and Oximes, Curr. Org. Chem., 2003, 7: 585-628
    • (2003) Curr. Org. Chem. , vol.7 , pp. 585-628
    • Koumbis, A.E.1    Gallos, J.K.2
  • 11
    • 0037404380 scopus 로고    scopus 로고
    • 1,3-dipolar cycloadditions in the synthesis of carbohydrate mimics. Part 3: Azides, diazo compounds and other dipoles
    • c) Koumbis A.E. and Gallos J.K., 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 3: Azides, Diazo Compounds and Other Dipoles, Curr. Org. Chem., 2003, 7: 771-797
    • (2003) Curr. Org. Chem. , vol.7 , pp. 771-797
    • Koumbis, A.E.1    Gallos, J.K.2
  • 12
    • 4444342151 scopus 로고    scopus 로고
    • Carbohydrates: From 'chirons' to new glycosubstances
    • Sharma G.V. M. and Krishna P.R., Carbohydrates: From 'Chirons' to New Glycosubstances, Curr. Org. Chem., 2004, 8: 1187-1209
    • (2004) Curr. Org. Chem. , vol.8 , pp. 1187-1209
    • Sharma, G.V.M.1    Krishna, P.R.2
  • 13
    • 0034175619 scopus 로고    scopus 로고
    • Synthesis of the C-glycosidic analog of adenophostin A, a potent IP3 receptor agonist, using a temporary silicon-tethered radical coupling reaction as the key step
    • Abe H., Shuto S. and Matsuda A., Synthesis of the C-glycosidic analog of adenophostin A, a potent IP3 receptor agonist, using a temporary silicon-tethered radical coupling reaction as the key step, Tetrahedron Lett., 2000, 41: 2391-2394
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2391-2394
    • Abe, H.1    Shuto, S.2    Matsuda, A.3
  • 14
    • 0034706359 scopus 로고    scopus 로고
    • Stereoselective synthesis of C-glycosides via Tebbe methylenation and Claisen rearrangement
    • Godage H.Y. and Fairbanks A.J., Stereoselective synthesis of C-glycosides via Tebbe methylenation and Claisen rearrangement, Tetrahedron Lett., 2000, 41: 7589-7593
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7589-7593
    • Godage, H.Y.1    Fairbanks, A.J.2
  • 15
    • 0037008981 scopus 로고    scopus 로고
    • Samarium diiodide-mediated reductive coupling of epoxides and carbonyl compounds: A stereocontrolled synthesis of C-glycosides from 1,2-anhydro sugars
    • Chiara J.L. and Sesmilo E., Samarium Diiodide-Mediated Reductive Coupling of Epoxides and Carbonyl Compounds: A Stereocontrolled Synthesis of C-Glycosides from 1,2-Anhydro Sugars, Angew. Chem. Int. Ed., 2002, 41: 3242-3246
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3242-3246
    • Chiara, J.L.1    Sesmilo, E.2
  • 16
    • 0034616213 scopus 로고    scopus 로고
    • Recent applications of olefin metathesis and related reactions in carbohydrate chemistry
    • Roy R. and Das S.K., Recent applications of olefin metathesis and related reactions in carbohydrate chemistry, Chem. Commun., 2000, 519-529
    • (2000) Chem. Commun. , pp. 519-529
    • Roy, R.1    Das, S.K.2
  • 17
    • 0036204489 scopus 로고    scopus 로고
    • A ramberg-bäcklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids
    • Paterson D.E., Griffin F.K., Alcaraz M.L. and Taylor R.J. K., A Ramberg-Bäcklund Approach to the Synthesis of C-Glycosides, C-Linked Disaccharides, and C-Glycosyl Amino Acids, Eur. J. Org. Chem., 2002, 1323-1336
    • (2002) Eur. J. Org. Chem. , pp. 1323-1336
    • Paterson, D.E.1    Griffin, F.K.2    Alcaraz, M.L.3    Taylor, R.J.K.4
  • 18
    • 0346786322 scopus 로고    scopus 로고
    • Conversion of diacetyl-C-(-D-glucopyranosyl) phloroglucinol to spiroketal compounds
    • Sato S., Kumazawa T., Watanabe K., Matsuba S. and Onodera J., Conversion of diacetyl-C-(-D-glucopyranosyl) phloroglucinol to spiroketal compounds, Carbohydr, Res., 2004, 339: 429-433
    • (2004) Carbohydr, Res. , vol.339 , pp. 429-433
    • Sato, S.1    Kumazawa, T.2    Watanabe, K.3    Matsuba, S.4    Onodera, J.5
  • 19
    • 0842283394 scopus 로고    scopus 로고
    • Synthesis of Cl-alkyl- and acylglycals from glycals using a B-alkyl Suzuki-Miyaura cross coupling approach
    • Potuzak J.S. and Tan D.S., Synthesis of Cl-alkyl- and acylglycals from glycals using a B-alkyl Suzuki-Miyaura cross coupling approach, Tetrahedron Lett. 2004, 45: 1797-1801
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1797-1801
    • Potuzak, J.S.1    Tan, D.S.2
  • 20
    • 0037964812 scopus 로고    scopus 로고
    • Stereoselective synthesis of substituted exo-glycals from 1-exo- Methylene pyranoses
    • Gómez A.M., Pedregosa A., Valverde S. and López J.C., Stereoselective synthesis of substituted exo-glycals from 1-exo- methylene pyranoses, Tetrahedron Lett., 2003, 44: 6111-6116
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6111-6116
    • Gómez, A.M.1    Pedregosa, A.2    Valverde, S.3    López, J.C.4
  • 21
    • 0036027099 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloaddition reactions of carbohydrate derived nitrones and oximes
    • Osborn H.M.I., Gemmell N. and Harwood L.M., 1,3-Dipolar cycloaddition reactions of carbohydrate derived nitrones and oximes, J. Chem. Soc., Perkin Trans. 1, 2002: 2419-2438
    • (2002) J. Chem. Soc., Perkin Trans. , vol.1 , pp. 2419-2438
    • Osborn, H.M.I.1    Gemmell, N.2    Harwood, L.M.3
  • 23
    • 0030951588 scopus 로고    scopus 로고
    • Synthesis of stable analogues of glyceroglycolipids
    • Cipolla L., Nicotra F., Vismara E. and Guerrini M., Synthesis of Stable Analogues of Glyceroglycolipids, Tetrahedron, 1997, 53: 6163-6170
    • (1997) Tetrahedron , vol.53 , pp. 6163-6170
    • Cipolla, L.1    Nicotra, F.2    Vismara, E.3    Guerrini, M.4
  • 24
    • 0033618291 scopus 로고    scopus 로고
    • Claisen-Ireland rearrangement: A new route to C-glycosides
    • Vidai T., Haudrechy A. and Langois Y., Claisen-Ireland rearrangement: a new route to C-glycosides, Tetrahedron Lett., 1999, 40: 5677-5670
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5677-15670
    • Vidai, T.1    Haudrechy, A.2    Langois, Y.3
  • 25
    • 0942277393 scopus 로고    scopus 로고
    • Synthesis and uses of exo-glycals
    • Taillefumier C. and Chapleur Y., Synthesis and Uses of exo-Glycals, Chem. Rev., 2004, 104: 263-292
    • (2004) Chem. Rev. , vol.104 , pp. 263-292
    • Taillefumier, C.1    Chapleur, Y.2
  • 26
    • 29444442296 scopus 로고    scopus 로고
    • Exo-glycal chemistry: General aspects and synthetic applications for biochemical use
    • Lin C.H., Lin H.C. and Yang W.B., exo-Glycal Chemistry: General Aspects and Synthetic Applications for Biochemical Use, Curr. Top. Med. Chem., 2005, 5: 1431
    • (2005) Curr. Top. Med. Chem. , vol.5 , pp. 1431
    • Lin, C.H.1    Lin, H.C.2    Yang, W.B.3
  • 30
    • 0035858616 scopus 로고    scopus 로고
    • An efficient synthesis of new 1'-C-methyl-O-D-disaccharides using 1-methylenesugars as the glycosyl donors
    • Li X.L., Ohtake H., Takahashi H. and Tkegami S., An efficient synthesis of new 1'-C-methyl-O-D-disaccharides using 1-methylenesugars as the glycosyl donors, Tetrahedron, 2001, 57: 4283-4295
    • (2001) Tetrahedron , vol.57 , pp. 4283-4295
    • Li, X.L.1    Ohtake, H.2    Takahashi, H.3    Tkegami, S.4
  • 31
    • 0035858735 scopus 로고    scopus 로고
    • A facile synthesis of 1'-C-alkyl-disaccharides from 1-C-alkyl- hexopyranoxes and methyl-1-C-alky-hexopyranosides
    • Li X.L., Ohtake H., Takahashi H. and Ikegami S., A facile synthesis of 1'-C-alkyl-disaccharides from 1-C-alkyl-hexopyranoxes and methyl-1-C-alky- hexopyranosides, Tetrahedron, 2001, 57: 4297-4309
    • (2001) Tetrahedron , vol.57 , pp. 4297-4309
    • Li, X.L.1    Ohtake, H.2    Takahashi, H.3    Ikegami, S.4
  • 32
    • 0035903883 scopus 로고    scopus 로고
    • Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides
    • Li X.L., Takahashi H., Ohtake H., Shiro M. and Ikegami S., Stereoselective synthesis and structure elucidation of spiro-ketodisaccharides, Tetrahedron, 2001, 57: 8053-8066
    • (2001) Tetrahedron , vol.57 , pp. 8053-8066
    • Li, X.L.1    Takahashi, H.2    Ohtake, H.3    Shiro, M.4    Ikegami, S.5
  • 33
    • 0025959623 scopus 로고
    • Methylenation of aldonolactones
    • Csuk R. and Glanzer R.I., Methylenation of Aldonolactones, Tetrahetron, 1991, 47: 1655-1664
    • (1991) Tetrahetron , vol.47 , pp. 1655-1664
    • Csuk, R.1    Glanzer, R.I.2
  • 34
    • 0037347466 scopus 로고    scopus 로고
    • Synthesis of ketosyl spiro-isoxazolin dine by 1,3-dipolar cycloaddition of 1-methylenesugars with nitrones - A new access to C-glycosyl amino acids
    • Li X.L., Takahashi H., Ohtake H. and Ikegami S., Synthesis of ketosyl spiro-isoxazolin dine by 1,3-dipolar cycloaddition of 1-methylenesugars with nitrones - a new access to C-glycosyl amino acids, Heterocycles, 2003, 59: 547-571
    • (2003) Heterocycles , vol.59 , pp. 547-571
    • Li, X.L.1    Takahashi, H.2    Ohtake, H.3    Ikegami, S.4
  • 35
    • 2342486159 scopus 로고    scopus 로고
    • 1,3-dipolar cycloaddition of exo- Methylenesugars with nitrone: Approach to new amino-C-ketosyl disaccharides
    • Li X.L., Takahashi H., Ohtake H. and Ikegami S., 1,3-Dipolar cycloaddition of exo- methylenesugars with nitrone: approach to new amino-C-ketosyl disaccharides, Tetrahedron Lett., 2004, 45:4123-4126
    • (2004) Tetrahedron Lett. , vol.45 , pp. 4123-4126
    • Li, X.L.1    Takahashi, H.2    Ohtake, H.3    Ikegami, S.4
  • 36
    • 0034699058 scopus 로고    scopus 로고
    • Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones
    • Gothelf K.V. and Jorgensen K.A., Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones, Chem. Commun., 2000, 1449-1458
    • (2000) Chem. Commun. , pp. 1449-1458
    • Gothelf, K.V.1    Jorgensen, K.A.2
  • 37
    • 0032554269 scopus 로고    scopus 로고
    • Modified nucleosides from nitrones: A new and efficient stereo-selective approach to isoxazolidinyl thymidine derivatives
    • Merino P., Frabco S., Graces N., Merchan F.L. and Tejero T., Modified nucleosides from nitrones: a new and efficient stereo-selective approach to isoxazolidinyl thymidine derivatives, Chem. Commun., 1998, 493
    • (1998) Chem. Commun. , pp. 493
    • Merino, P.1    Frabco, S.2    Graces, N.3    Merchan, F.L.4    Tejero, T.5
  • 38
    • 0033824386 scopus 로고    scopus 로고
    • Stereodivergent approaches to the synthesis of isoxazolidine analogues of r-amino acid nucleosides. Total synthesis of isoxazolidinyl deoxypolyoxin C and uracil polyoxin C
    • Merino P., Franco S., Merchan F.L. and Tejero T., Stereodivergent Approaches to the Synthesis of Isoxazolidine Analogues of r-Amino Acid Nucleosides. Total Synthesis of Isoxazolidinyl Deoxypolyoxin C and Uracil Polyoxin C, J. Org. Chem., 2000, 65: 5575-5589
    • (2000) J. Org. Chem. , vol.65 , pp. 5575-5589
    • Merino, P.1    Franco, S.2    Merchan, F.L.3    Tejero, T.4
  • 39
    • 0032542175 scopus 로고    scopus 로고
    • Ti(IV) promoted 1,3-dipolar cycloaddition of nitrones to vinyl ethers
    • Bayon P., March P., Figueredo M. and Font J., Ti(IV) Promoted 1,3-Dipolar Cycloaddition of Nitrones to Vinyl Ethers, Tetrahedron, 1998, 54: 15691-15700
    • (1998) Tetrahedron , vol.54 , pp. 15691-15700
    • Bayon, P.1    March, P.2    Figueredo, M.3    Font, J.4
  • 40
    • 0002379864 scopus 로고
    • Stereospecific synthesis of ethyl (2-acetamido-2-deoxy-α-D- glucopyranosyl)-acetate
    • Nicotra F., Russo G, Ronchetti F. and Toma L., Stereospecific synthesis of ethyl (2-acetamido-2-deoxy-α-D-glucopyranosyl)-acetate, Carbohydr. Res., 1983, 124: C5-C7
    • (1983) Carbohydr. Res. , vol.124
    • Nicotra, F.1    Russo, G.2    Ronchetti, F.3    Toma, L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.