Stereoselective Synthesis of α-Keto-deoxy-D-glycero-D-galacto-nonulosonic Acid Glycosides by Means of the 4,5-O-Carbonate Protecting Group

被引：32

作者：

Crich, David ^{[1
,2
]}

Navuluri, Chandrasekhar ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

[2] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91128 Gif Sur Yvette, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 17期

关键词：

carbonate; glycosylation; sialic acid; stereoselectivity; thioglycoside; N-GLYCOLYLNEURAMINIC ACID; GLYCOSYLATION REACTIONS; SELECTIVE SIALYLATIONS; ACETYLNEURAMINIC ACID; SIALIC-ACID; KDN; OLIGOSACCHARIDES; SOLVENTS; FACILE;

D O I：

10.1002/anie.200907178

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Figure Presented) Unrivaled: A 1-adamantyl thioglycoside derivative of the nonulosonic acid KDN, carrying a 4,5-O-carbonate protecting group, is a highly efficient and a-selective KDN donor when activated using N-iodosuccinimide (NIS) and trifluoromethanesulfonic acid (TfOH). Glycosylates conducted with this protecting group do not suffer from competing glycal formation. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：3049 / 3052

页数：4