Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-alpha-L-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D

Qian Yang; Ming Lei; Qin-Jian Yin; Jin-Song Yang

doi:10.1016/j.carres.2007.03.001

Silver(I) oxide-mediated regioselective 2-monoacylation in 3-O-benzyl-alpha-L-rhamnopyranosides and application in synthesis of a protected tetrasaccharide fragment of potent cytotoxic saponins gleditsiosides C and D

Carbohydr Res. 2007 Jul 2;342(9):1175-81. doi: 10.1016/j.carres.2007.03.001. Epub 2007 Mar 6.

Authors

Qian Yang¹, Ming Lei, Qin-Jian Yin, Jin-Song Yang

Affiliation

¹ Department of Chemistry of Medicinal Natural Products and Key Laboratory of Drug Targeting of the Ministry of Education, School of Pharmacy, Sichuan University, Chengdu 610041, PR China.

PMID: 17379197
DOI: 10.1016/j.carres.2007.03.001

Abstract

The axial 2-hydroxyl group of methyl and allyl 3-O-benzyl-alpha-L-rhamnopyranosides was selectively acylated in 56-78% yields by reaction with 1.1 equiv of acyl chloride in the presence of 1.5 equiv of silver(I) oxide. Use of the method permitted a convenient synthesis of a protected tetrasaccharide fragment of triterpene saponins gleditsiosides C and D.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acylation
Carbohydrate Conformation
Carbohydrate Sequence
Glucosides / chemical synthesis*
Glucosides / chemistry
Models, Molecular
Molecular Structure
Oligosaccharides / chemical synthesis*
Oligosaccharides / chemistry
Oxides / chemistry*
Rhamnose / chemistry
Saponins / chemical synthesis*
Saponins / chemistry
Silver Compounds / chemistry*
Stereoisomerism

Substances

Glucosides
Oligosaccharides
Oxides
Saponins
Silver Compounds
disilver oxide
Rhamnose