Stereoselective synthesis and crystal structure of 4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride  

作　　者：Fu Yi Zhang Chun Li Wu Cui Zhang Hong Min Liu 

机构地区：[1]Chemistry Department,The Key Lab of Chemical Biology and Organic Chemistry of Henan Province,Zhengzhou University, Zhengzhou 450052,China [2]School of Pharmaceutical Sciences,Zhengzhou University,Zhengzhou 450001,China

出　　处：《Chinese Chemical Letters》2010年第7期798-801,共4页中国化学快报（英文版）

基　　金：the financial supports from the National Natural Science Foundation of China(No. 20972142);the State Key Laboratory of Bio-organic and Natural Products Chemistry,CAS(No.08417).

摘　　要：The building block of N-alkyl derivative of allosamidin（chitinase inhibitor）,4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride was stereoselectively synthesized in two steps under mild conditions.Nucleophilic addition of octylamine to 2- oxoglucopyranoside gave a‘carbonyl group transfer＇ product in 62%yield.Subsequent stereoselective reduction of newly formed C=O with NaBH_4 produced title compound in 75%yield.X-ray diffraction analysis indicates the title compound adopts syn 1,2,3 stereochemistry and chair-chair conformation.The crystal structure is stabilized by hydrogen bonds.The building block of N-alkyl derivative of allosamidin（chitinase inhibitor）,4,6-O-benzylidene-N-octyl-D-allosamine hydrochloride was stereoselectively synthesized in two steps under mild conditions.Nucleophilic addition of octylamine to 2- oxoglucopyranoside gave a‘carbonyl group transfer＇ product in 62%yield.Subsequent stereoselective reduction of newly formed C=O with NaBH_4 produced title compound in 75%yield.X-ray diffraction analysis indicates the title compound adopts syn 1,2,3 stereochemistry and chair-chair conformation.The crystal structure is stabilized by hydrogen bonds.

关 键 词：2-Oxoglucopyranoside 4 6-O-benzylidene-N-octyl-D-allosamine hydrochloride X-ray structure 

分 类 号：TQ453.4[化学工程—农药化工] O614.121[理学—无机化学]