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.