(620c) Synthesis of Drug Intermediates By Monoprotection of Diols in C-Glycosides

Synthesis of Drug Intermediates by Monoprotection
of Diols in C-GlycosidesADDIN
IUCrAuthors

Tao Zhang and Zhijie Fang*

School of Chemical Engineering, Nanjing
University of Science & Technology

Correspondence email: zjfang@njust.edu.cn

Abstract:
Selective and per-O-esterification of carbohydrate
derivatives using acyl chloride or anhydride and DMAP
(4-dimethylaminopyridine), were first systematically reported. This was a
common protocol that only one monoprotected product
could be obtained by the screening of esterification reagents. For result
confirmation, nuclear magnetic resonance study and theoretical calculation
approach were set out to analyze and support the results i.e. 3-Ts (compound
6j) was the only per-O-substituted product when TsCl
(4-toluene sulfonyl chloride) was used as
esterification reagent. The research will be used as a quick and easy method to
the application of synthesis of carbohydrate drugs.