Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst

Ming-Chung Yan; Yeng-Nan Chen; Huan-Ting Wu; Chang-Ching Lin; Chien-Tien Chen; Chun-Cheng Lin

doi:10.1021/jo061881g

Removal of acid-labile protecting groups on carbohydrates using water-tolerant and recoverable vanadyl triflate catalyst

J Org Chem. 2007 Jan 5;72(1):299-302. doi: 10.1021/jo061881g.

Authors

Ming-Chung Yan¹, Yeng-Nan Chen, Huan-Ting Wu, Chang-Ching Lin, Chien-Tien Chen, Chun-Cheng Lin

Affiliation

¹ Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan.

PMID: 17194117
DOI: 10.1021/jo061881g

Abstract

Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.

Publication types

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

MeSH terms

Acids / chemistry*
Alkenes / chemistry
Benzylidene Compounds / chemistry
Carbohydrates / chemistry*
Catalysis
Mesylates / chemistry*
Molecular Structure
Vanadates / chemistry*
Water / chemistry*

Substances

Acids
Alkenes
Benzylidene Compounds
Carbohydrates
Mesylates
vanadyl triflate
Water
Vanadates
propylene