One-step synthesis of β-C-glycosidic ketones in aqueous media:: The case of 2-acetamido sugars

被引：49
作者：
Bragnier, N [1 ]
Scherrmann, MC [1 ]
机构：
[1] Univ Paris 11, Lab Chim Organ Multifonct, F-91405 Orsay, France
来源：
SYNTHESIS-STUTTGART | 2005年 / 05期
关键词：
asymmetric synthesis; carbohydrates; condensation; C-glycosides; ketones;
D O I：
10.1055/s-2005-861816
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The one step synthesis of beta-D-C-glycosidic ketones by condensation of pentane-2,4-dione with unprotected N-acetyl-D-gluco-, manno-, and galactosamine in alkaline aqueous media has been explored. N-Acetyl-D-gluco- and mannosamine gave, in good yield, a mixture of the two gluco and manno C-glycosidic ketones, which were separated by crystallization after acetylation, whereas N-acetyl-D-galactosamine afforded the galacto C-glycosidic ketone which was isolated as its acetylated derivative in 50% yield.
引用
收藏
页码：814 / 818
页数：5
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