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.
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页码：6288 / 6291
页数：4
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