A New Approach to Neuraminic Acid Analogues via 1,2-Oxazines

被引：43

作者：

Bressel, Bettina ^{[1
]}

Reissig, Hans-Ulrich ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 03期

关键词：

N-ACETYLNEURAMINIC ACID; GLUCONO-DELTA-LACTONE; ENANTIOPURE 3,6-DIHYDRO-2H-1,2-OXAZINES; AMINO ALDEHYDES; SIALIC-ACID; SIDE-CHAIN; O BONDS; DERIVATIVES; CLEAVAGE; INHIBITORS;

D O I：

10.1021/ol802514m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new stereoselective and potentially very flexible (C-5 + C-3 + C-1) approach to neuraminic acid derivatives and analogues has been established using enantiopure nitrones and alkoxyallenes as C-3 and C-1 building blocks. Substituent OR2 in position 4 of neuraminic acid analogues is defined by the alkoxyallene employed for the synthesis of the intermediate 1,2-oxazine. Side chain R-1 can be varied by using different precursor nitrones and introduction of different protection groups R-3 at the amino function is also possible.

引用

页码：527 / 530

页数：4

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