Functional Group Tolerance in Organocatalytic Regioselective Acylation of Carbohydrates
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- 作者：Yoshihiro Ueda ; Wataru Muramatsu ; Kenji Mishiro ; Takumi Furuta ; Takeo Kawabata
- 刊名：Journal of Organic Chemistry
- 出版年：2009
- 出版时间：November 20, 2009
- 年：2009
- 卷：74
- 期：22
- 页码：8802-8805
- 全文大小：789K
- 年卷期：v.74,no.22(November 20, 2009)
- ISSN：1520-6904
文摘
Organocatalytic regioselective acylation of mono- and disaccaharides with various functionalized acid anhydrides has been developed. Acylation of octyl β-d-glucopyranoside with acid anhydrides derived from α-amino acids, cinnamic acid, and gallic acid took place at C(4)-OH with 67−94% regioselectivity in the presence of catalyst 1. Regioselective acylation of disaccharides with functionalized acid anhydrides was also achieved with 78−94% selectivity. Especially, a disaccharide with seven free hydroxy groups (X = OH, R′ = H) underwent acylation at C(4)-OH with 78% regioselectivity in the presence of 1. Thus, functional group tolerance in the regioselective acylation catalyzed by 1 was found to be high.