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Volumn 3, Issue 8-9, 2008, Pages 1664-1677

Catalytic stereoselective glycosidation with glycosyl diphenyl phosphates: Rapid construction of 1,2-cis-α-glycosidic linkages

Author keywords

Carbohydrates; Glycosylation; Perchloric acid; Phosphates; Stereoselectivity

Indexed keywords

ALCOHOL DERIVATIVE; BIPHENYL; BIPHENYL DERIVATIVE; GLYCOSIDE; PHOSPHATE; SOLVENT;

EID: 54849424559     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200800173     Document Type: Article
Times cited : (33)

References (154)
  • 1
    • 5244279498 scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: a) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531;
    • (1993) Chem. Rev , vol.93 , pp. 1503-1531
    • Toshima, K.1    Tatsuta, K.2
  • 3
    • 0004111999 scopus 로고    scopus 로고
    • Eds, S. H. Khan, R. A. O'Neil, Harwood Academic Publishers, Amsterdam
    • c) Modern Methods in Carbohydrate Synthesis (Eds.: S. H. Khan, R. A. O'Neil), Harwood Academic Publishers, Amsterdam, 1996;
    • (1996) Modern Methods in Carbohydrate Synthesis
  • 4
    • 0004055174 scopus 로고    scopus 로고
    • Eds, B. Ernst, G. W. Hart, P. Sinaÿ, VCH, Weinheim, Part I;
    • d) Carbohydrates in Chemistry and Biology (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), VCH, Weinheim, 2000, Part I;
    • (2000) Carbohydrates in Chemistry and Biology
  • 7
    • 0037247972 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: a) A. V. Demchenko, Curr. Org. Chem. 2003, 7, 35-79;
    • (2003) Curr. Org. Chem , vol.7 , pp. 35-79
    • Demchenko, A.V.1
  • 9
    • 24144498474 scopus 로고    scopus 로고
    • Very recently, the (1S)-phenyl-2-(phenylsulfanyl)ethyl group was developed as an O-2 protecting group with an anchimeric assistance for the exclusive formation of α-glycosides: J.-H. Kim, H. Yang, J. Park, G.-J. Boons, J. Am. Chem. Soc. 2005, 127, 12090-12097.
    • Very recently, the (1S)-phenyl-2-(phenylsulfanyl)ethyl group was developed as an O-2 protecting group with an anchimeric assistance for the exclusive formation of α-glycosides: J.-H. Kim, H. Yang, J. Park, G.-J. Boons, J. Am. Chem. Soc. 2005, 127, 12090-12097.
  • 10
    • 0042671098 scopus 로고    scopus 로고
    • Kiso and co-workers reported that the 4,6-O-di-tert-butylsilylene-protected galactosyl and galactosaminyl donors exhibited good to excellent a selectivities despite the presence of C-2 functionalities capable of neighboring group participation: a A. Imamura, H. Ando, S. Korogi, G. Tanabe, O. Muraoka, H. Ishida, M. Kiso, Tetrahedron Lett. 2003, 44, 6725-6728;
    • Kiso and co-workers reported that the 4,6-O-di-tert-butylsilylene-protected galactosyl and galactosaminyl donors exhibited good to excellent a selectivities despite the presence of C-2 functionalities capable of neighboring group participation: a) A. Imamura, H. Ando, S. Korogi, G. Tanabe, O. Muraoka, H. Ishida, M. Kiso, Tetrahedron Lett. 2003, 44, 6725-6728;
  • 13
    • 0015970036 scopus 로고
    • For reviews that include discussions regarding the effect of ethereal solvents, see: a
    • For reviews that include discussions regarding the effect of ethereal solvents, see: a) G. Wulff, G. Röhle, Angew. Chem. 1974, 86, 173-187;
    • (1974) Angew. Chem , vol.86 , pp. 173-187
    • Wulff, G.1    Röhle, G.2
  • 16
    • 48749140248 scopus 로고
    • For representative examples of the use of ether, which leads to the formation of an α-glycosidic linkage, see: a
    • For representative examples of the use of ether, which leads to the formation of an α-glycosidic linkage, see: a) S. Hashimoto, M. Hayashi, R. Noyori, Tetrahedron Lett. 1984, 25, 1379-1382;
    • (1984) Tetrahedron Lett , vol.25 , pp. 1379-1382
    • Hashimoto, S.1    Hayashi, M.2    Noyori, R.3
  • 20
    • 0242631685 scopus 로고    scopus 로고
    • 2O: a K. Igarashi, T. Honma, J. Irisawa, Carbohydr. Res. 1970, 15, 329-337;
    • 2O: a) K. Igarashi, T. Honma, J. Irisawa, Carbohydr. Res. 1970, 15, 329-337;
  • 47
    • 0037124658 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 2128-2131.
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 2128-2131
  • 52
  • 55
    • 0001409217 scopus 로고    scopus 로고
    • For the use of P,P-diphenyl-N-(p-toluenesulfonyl) phosphinimidate as a leaving group, see: a) S. Hashimoto, T. Honda, S. Ikegami, Heterocycles 1990, 30, 775-778;
    • For the use of P,P-diphenyl-N-(p-toluenesulfonyl) phosphinimidate as a leaving group, see: a) S. Hashimoto, T. Honda, S. Ikegami, Heterocycles 1990, 30, 775-778;
  • 58
    • 0025327537 scopus 로고    scopus 로고
    • For the use of N,N,N′,N′-tetramethyl-N″-phenylphosphorodiamidimidothioate as a leaving group, see: S. Hashimoto, T. Honda, S. Ikegami, Tetrahedron Lett. 1990, 31, 4769-4772.
    • For the use of N,N,N′,N′-tetramethyl-N″-phenylphosphorodiamidimidothioate as a leaving group, see: S. Hashimoto, T. Honda, S. Ikegami, Tetrahedron Lett. 1990, 31, 4769-4772.
  • 59
    • 0026780175 scopus 로고    scopus 로고
    • For the use of N,N,N′,N′- tetramethylphosphorodiamidate as a leaving group, see: a S. Hashimoto, Y. Yanagiya, T. Honda, H. Harada, S. Ikegami, Tetrahedron Lett. 1992, 33, 3523-3526;
    • For the use of N,N,N′,N′- tetramethylphosphorodiamidate as a leaving group, see: a) S. Hashimoto, Y. Yanagiya, T. Honda, H. Harada, S. Ikegami, Tetrahedron Lett. 1992, 33, 3523-3526;
  • 70
    • 17644412385 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 2245-2249;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 2245-2249
  • 72
    • 0030848902 scopus 로고    scopus 로고
    • For chemoselective glycosidation strategies capitalizing on phosphorus-containing leaving groups, see: a
    • For chemoselective glycosidation strategies capitalizing on phosphorus-containing leaving groups, see: a) S. Hashimoto, H. Sakamoto, T. Honda, S. Ikegami, Tetrahedron Lett. 1997, 38, 5181-5184;
    • (1997) Tetrahedron Lett , vol.38 , pp. 5181-5184
    • Hashimoto, S.1    Sakamoto, H.2    Honda, T.3    Ikegami, S.4
  • 75
    • 0004055174 scopus 로고    scopus 로고
    • For reviews on glycosidations of glycosyl phosphates, phosphites and other O-P derivatives, see: a, Eds, B. Ernst, G. W. Hart, P. Sinaÿ, VCH, Weinheim, Part I, pp
    • For reviews on glycosidations of glycosyl phosphates, phosphites and other O-P derivatives, see: a) Z. Zhang, C.-H. Wong in Carbohydrates in Chemistry and Biology (Eds.: B. Ernst, G. W. Hart, P. Sinaÿ), VCH, Weinheim, 2000, Part I, pp. 117-134;
    • (2000) Carbohydrates in Chemistry and Biology , pp. 117-134
    • Zhang, Z.1    Wong, C.-H.2
  • 81
    • 0002869847 scopus 로고    scopus 로고
    • Glycosyl iodides were prepared and used as donors for the preparation of α-glycosides: a F. J. Kronzer, C. Schuerch, Carbohydr. Res. 1974, 34, 71- 78;
    • Glycosyl iodides were prepared and used as donors for the preparation of α-glycosides: a) F. J. Kronzer, C. Schuerch, Carbohydr. Res. 1974, 34, 71- 78;
  • 84
    • 0037144691 scopus 로고    scopus 로고
    • 2O (1:4) at low temperature (-78→-20°C), but the scope of the reaction has not been explored: F. Bosse, L. A. Marcaurelle, P. H. Seeberger, J. Org. Chem. 2002, 67, 6659-6670.
    • 2O (1:4) at low temperature (-78→-20°C), but the scope of the reaction has not been explored: F. Bosse, L. A. Marcaurelle, P. H. Seeberger, J. Org. Chem. 2002, 67, 6659-6670.
  • 87
    • 33751157840 scopus 로고
    • For the use of Brønsted acids as promoters in glycosidations with glycosyl phosphites, see: a
    • For the use of Brønsted acids as promoters in glycosidations with glycosyl phosphites, see: a) H. Kondo, S. Aoki, Y. Ichikawa, R. L. Halcomb, H. Ritzen, C.-H. Wong, J. Org. Chem. 1994, 59, 864-877;
    • (1994) J. Org. Chem , vol.59 , pp. 864-877
    • Kondo, H.1    Aoki, S.2    Ichikawa, Y.3    Halcomb, R.L.4    Ritzen, H.5    Wong, C.-H.6
  • 88
    • 54849425128 scopus 로고    scopus 로고
    • reference [19e];
    • b) reference [19e];
  • 89
    • 54849409464 scopus 로고    scopus 로고
    • 4 to activate a glycosyl diethyl phosphite, see reference [19 h].
    • 4 to activate a glycosyl diethyl phosphite, see reference [19 h].
  • 90
    • 54849425753 scopus 로고    scopus 로고
    • The remarkable α-directing effect of dioxane has already been documented by Boons and co-workers: a reference [9f];
    • The remarkable α-directing effect of dioxane has already been documented by Boons and co-workers: a) reference [9f];
  • 91
    • 54849406979 scopus 로고    scopus 로고
    • reference [9i
    • b) reference [9i].
  • 92
    • 0035802334 scopus 로고    scopus 로고
    • Seeberger and co-workers demonstrated that the glycosidation reaction of a glycosyl dibutyl phosphate with a TMS ether proceeded to completion by the use of 1 mol% of TfOH as a promoter, since TMSOTf, generated in situ along with the desilylated alcohol, functioned as an actual promoter for the formation of the 1,2-trans-β-glycoside from glycosyl dibutyl phosphate: O. J. Plante, E. R. Palmacci, R. B. Andrade, P. H. Seeberger, J. Am. Chem. Soc. 2001, 123, 9545-9554
    • Seeberger and co-workers demonstrated that the glycosidation reaction of a glycosyl dibutyl phosphate with a TMS ether proceeded to completion by the use of 1 mol% of TfOH as a promoter, since TMSOTf, generated in situ along with the desilylated alcohol, functioned as an actual promoter for the formation of the 1,2-trans-β-glycoside from glycosyl dibutyl phosphate: O. J. Plante, E. R. Palmacci, R. B. Andrade, P. H. Seeberger, J. Am. Chem. Soc. 2001, 123, 9545-9554.
  • 93
    • 54849411232 scopus 로고    scopus 로고
    • 4 solution in the reaction of diethyl phosphite 2 with alcohol 3 exhibited diminished α selectivity (α/β= 85:15), again demonstrating the superiority of phosphate 1 over phosphite 2.
    • 4 solution in the reaction of diethyl phosphite 2 with alcohol 3 exhibited diminished α selectivity (α/β= 85:15), again demonstrating the superiority of phosphate 1 over phosphite 2.
  • 98
    • 54849437489 scopus 로고    scopus 로고
    • A control experiment revealed that anomer equilibration of diphenyl phosphate 1 (α/β=1:99) was effected within 30 seconds under the optimized conditions to give a 98:2 equilibrium mixture in favor of the thermodynamically more stable α anomer 1α.
    • A control experiment revealed that anomer equilibration of diphenyl phosphate 1 (α/β=1:99) was effected within 30 seconds under the optimized conditions to give a 98:2 equilibrium mixture in favor of the thermodynamically more stable α anomer 1α.
  • 99
    • 54849409874 scopus 로고    scopus 로고
    • [31a]
    • [31a]
  • 100
    • 54849433789 scopus 로고    scopus 로고
    • Glycosidation of phosphate 1 with reactive alcohol 3 proceeded to 90% conversion during the 30 s period.
    • Glycosidation of phosphate 1 with reactive alcohol 3 proceeded to 90% conversion during the 30 s period.
  • 102
    • 0033518559 scopus 로고    scopus 로고
    • Wong and co-workers reported that the per-O-benzyl-protected thiogalactoside is 6.4-fold more active than the corresponding thioglucoside probably owing to the stereo- and inductive effects and possible involvement of the axial 4-O lone pair electrons in the stabilization of the oxocarbenium ion intermediate: Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734-753.
    • Wong and co-workers reported that the per-O-benzyl-protected thiogalactoside is 6.4-fold more active than the corresponding thioglucoside probably owing to the stereo- and inductive effects and possible involvement of the axial 4-O lone pair electrons in the stabilization of the oxocarbenium ion intermediate: Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov, C.-H. Wong, J. Am. Chem. Soc. 1999, 121, 734-753.
  • 103
    • 54849432585 scopus 로고    scopus 로고
    • 2Cl>-NPhth>-OBz>-OBn.
    • 2Cl>-NPhth>-OBz>-OBn.
  • 114
    • 54849430151 scopus 로고    scopus 로고
    • Kirin group: a reference [39a];
    • Kirin group: a) reference [39a];
  • 116
    • 0032568385 scopus 로고    scopus 로고
    • Mori group: c H. Takikawa, S. Muto, K. Mori, Tetrahedron 1998, 54, 3141-3150;
    • Mori group: c) H. Takikawa, S. Muto, K. Mori, Tetrahedron 1998, 54, 3141-3150;
  • 117
    • 0038399264 scopus 로고    scopus 로고
    • Schmidt group: d S. Figueroa-Pérez, R. R. Schmidt, Carbohydr. Res. 2000, 328, 95- 102;
    • Schmidt group: d) S. Figueroa-Pérez, R. R. Schmidt, Carbohydr. Res. 2000, 328, 95- 102;
  • 118
    • 0037189212 scopus 로고    scopus 로고
    • Wong group: e O. Plettenburg, V. Bodmer-Narkevitch, C.-H. Wong, J. Org. Chem. 2002, 67, 4559-4564;
    • Wong group: e) O. Plettenburg, V. Bodmer-Narkevitch, C.-H. Wong, J. Org. Chem. 2002, 67, 4559-4564;
  • 119
    • 54849423000 scopus 로고    scopus 로고
    • Kim group: f S. Kim, S. Song, T. Lee, S. Jung, D. Kim, Synthesis 2004, 847-850;
    • Kim group: f) S. Kim, S. Song, T. Lee, S. Jung, D. Kim, Synthesis 2004, 847-850;
  • 120
    • 54849412071 scopus 로고    scopus 로고
    • Lin group: g G.-T. Fan, Y. Pan, K.-C. Lu, Y.-P. Cheng, W.-C. Lin, S. Lin, C.-H. Lin, C.-H. Wong, J.-M. Fang, C.-C. Lin, Tetrahedron 2005, 61, 1855-1862;
    • Lin group: g) G.-T. Fan, Y. Pan, K.-C. Lu, Y.-P. Cheng, W.-C. Lin, S. Lin, C.-H. Lin, C.-H. Wong, J.-M. Fang, C.-C. Lin, Tetrahedron 2005, 61, 1855-1862;
  • 121
    • 19544385277 scopus 로고    scopus 로고
    • Gervay-Hague group: h W. Du, J. Gervay-Hague, Org. Lett. 2005, 7, 2063-2065;
    • Gervay-Hague group: h) W. Du, J. Gervay-Hague, Org. Lett. 2005, 7, 2063-2065;
  • 122
    • 32144457341 scopus 로고    scopus 로고
    • Hung group: i S.-Y. Luo, S. S. Kulkarni, C.-H. Chou, W.-M. Liao, S.-C. Hung, J. Org. Chem. 2006, 71, 1226-1229;
    • Hung group: i) S.-Y. Luo, S. S. Kulkarni, C.-H. Chou, W.-M. Liao, S.-C. Hung, J. Org. Chem. 2006, 71, 1226-1229;
  • 123
    • 33644788298 scopus 로고    scopus 로고
    • Wang group: j C. Xia, Q. Yao, J. Schümann, E. Rossy, W. Chen, L. Zhu, W. Zhang, G. De Libero, P. G. Wang, Bioorg. Med. Chem. Lett. 2006, 16, 2195-2199;
    • Wang group: j) C. Xia, Q. Yao, J. Schümann, E. Rossy, W. Chen, L. Zhu, W. Zhang, G. De Libero, P. G. Wang, Bioorg. Med. Chem. Lett. 2006, 16, 2195-2199;
  • 124
    • 33749344100 scopus 로고    scopus 로고
    • Kiso group: k A. Kimura, A. Imamura, H. Ando, H. Ishida, M. Kiso, Synlett 2006, 2379-2382;
    • Kiso group: k) A. Kimura, A. Imamura, H. Ando, H. Ishida, M. Kiso, Synlett 2006, 2379-2382;
  • 125
    • 33750628134 scopus 로고    scopus 로고
    • Painter group: l A. Lee, K. J. Farrand, N. Dickgreber, C. M. Hayman, S. Jürs, I. F. Hermans, G. F. Painter, Carbohydr. Res. 2006, 341, 2785-2798;
    • Painter group: l) A. Lee, K. J. Farrand, N. Dickgreber, C. M. Hayman, S. Jürs, I. F. Hermans, G. F. Painter, Carbohydr. Res. 2006, 341, 2785-2798;
  • 126
    • 34347401668 scopus 로고    scopus 로고
    • Ito group: m T. Tsujimoto, Y. Ito, Tetrahedron Lett. 2007, 48, 5513-5516.
    • Ito group: m) T. Tsujimoto, Y. Ito, Tetrahedron Lett. 2007, 48, 5513-5516.
  • 132
    • 0006644455 scopus 로고
    • For evidence supporting formation of oxonium ion intermediates by participation of THF, see: a
    • For evidence supporting formation of oxonium ion intermediates by participation of THF, see: a) B. Helferich, J. Zirner, Chem. Ber. 1963, 96, 374;
    • (1963) Chem. Ber , vol.96 , pp. 374
    • Helferich, B.1    Zirner, J.2


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