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
收藏
页码：3049 / 3052
页数：4
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