Rapid assembly of oligosaccharides: 1,2-diacetal-mediated reactivity tuning in the coupling of glycosyl fluorides

被引：60

作者：

Baeschlin, DK ^{[1
]}

Green, LG ^{[1
]}

Hahn, MG ^{[1
]}

Hinzen, B ^{[1
]}

Ince, SJ ^{[1
]}

Ley, SV ^{[1
]}

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 01期

基金：

英国工程与自然科学研究理事会; 英国生物技术与生命科学研究理事会;

关键词：

D O I：

10.1016/S0957-4166(99)00519-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

This paper describes the application of 1,2-diacetal protecting groups to control the reactivity tuning of glycosyl fluorides in oligosaccharide coupling reactions. The synthetic potential of this new methodology is demonstrated by the 'one-pot' synthesis of a linear pentasaccharide and the efficient assembly of the core oligosaccharide of the GPI anchor of yeast (Saccharomyces cerevisiae). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：173 / 197

页数：25

共 85 条

[1] OSMIUM-MEDIATED ASYMMETRIC-SYNTHESIS OF GLYCOSYL-MYO-INOSITOLS FROM OXANORBORNANES
ARJONA, O
CANDILEJO, A
DEDIOS, A
DELAPRADILLA, RF
PLUMET, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (23) : 6097 - 6099
[2] Baeschlin DK, 2000, CHEM-EUR J, V6, P172, DOI 10.1002/(SICI)1521-3765(20000103)6:1<172::AID-CHEM172>3.3.CO
[3] 2-X
[4] Baeschlin DK, 1998, ANGEW CHEM INT EDIT, V37, P3423, DOI [10.1002/(SICI)1521-3773(19981231)37:24&lt
[5] 3423::AID-, 10.1002/(SICI)1521-3773(19981231)37:24<3423::AID-ANIE3423>3.0.CO
[6] 2-I]
[7] A SIMPLE AND EFFECTIVE CHEMICAL PHOSPHORYLATION PROCEDURE FOR BIOMOLECULES
BANNWARTH, W
TRZECIAK, A
[J]. HELVETICA CHIMICA ACTA, 1987, 70 (01) : 175 - 186
[8] Barrena MI, 1996, SYNLETT, P675
[9] DISPIROKETALS IN SYNTHESIS .5. A NEW OPPORTUNITY FOR OLIGOSACCHARIDE SYNTHESIS USING DIFFERENTIALLY ACTIVATED GLYCOSYL DONORS AND ACCEPTORS
BOONS, GJ
GRICE, P
LESLIE, R
LEY, SV
YEUNG, LL
[J]. TETRAHEDRON LETTERS, 1993, 34 (52) : 8523 - 8526
[10] Boons GJ, 1997, SYNLETT, P809

← 1 2 3 4 5 6 7 8 9 →