Practical Synthesis of 2-Keto-3-deoxy-D-glycero-D-galactononulosonic Acid (KDN)

被引：14

作者：

Crich, David ^{[1
]}

Navuluri, Chandrasekhar ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 23期

关键词：

N-ACETYLNEURAMINIC ACID; SIALIC ACIDS;

D O I：

10.1021/ol202773t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-Isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the alpha-keto acid moiety from the alkyne.

引用

页码：6288 / 6291

页数：4

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