Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology

被引：10
作者：
Park, Simon S. [1 ]
Gervay-Hague, Jacquelyn [1 ]
机构：
[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 19期
基金：
美国国家卫生研究院;
关键词：
SIALIC ACIDS; EFFICIENT; SUGARS;
D O I：
10.1021/ol502389g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synthesized. Reaction of per-O-silylated Neu5Ac ester with AcOH and Ac2O in pyridine promotes regioselective silyl ether/acetate exchange in the following order: C-4 (2 degrees) > C-9 (1 degrees) > C-8 (2 degrees) > C-2 (anomeric). Subsequent hydrogenolysis affords the corresponding sialic acid analogues as useful chemical biology tools.
引用
收藏
页码：5044 / 5047
页数：4
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