使用 1,2-环丙烷乙酰化糖作为新型糖基供体立体选择性合成 2-C-乙酰基-2-脱氧-D-半乳糖苷。

Stereoselective synthesis of 2-C-acetonyl-2-deoxy-D-galactosides using 1,2-cyclopropaneacetylated sugar as novel glycosyl donor.

机构信息

Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China.

出版信息

Org Lett. 2010 Feb 5;12(3):540-3. doi: 10.1021/ol902732w.

PMID:20041707

Abstract

1,2-Cyclopropaneacetylated sugar is an effective glycosyl donor, which reacted with various glycosyl acceptors including monosaccharides, amino acids and other alcohols in the presence of BF(3)*OEt(2) or TMSOTf. The glycosylation is stereoselective in favor of beta-anomeric products with BF(3)*OEt(2) as catalyst, whereas TMSOTf-catalyzed glycosylation prefers the alpha-anomeric products. 2-C-Acetonyl-2-deoxy-D-galactosides were obtained in good yields.

摘要

1,2-环丙基乙酰化糖是一种有效的糖基供体，在 BF(3)*OEt(2) 或 TMSOTf 的存在下，可与各种糖基受体反应，包括单糖、氨基酸和其他醇。BF(3)*OEt(2) 作为催化剂时，糖苷化具有立体选择性，有利于β-端基产物，而 TMSOTf 催化的糖苷化则优先生成α-端基产物。2-C-乙酰基-2-脱氧-D-半乳糖苷以良好的产率得到。