First Synthesis of a Series of New Natural Glucosides  

作　　者：屈孟男 周岭 曹小平 

机构地区：[1]State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, Gansu 730000, China

出　　处：《Chinese Journal of Chemistry》2006年第11期1625-1630,共6页中国化学（英文版）

基　　金：Project supported by the National Natural Science Foundation of China （Nos. 20472025 and QT 20021001）.

摘　　要：Alkyl glucoside 1 and aryl glycosides 2-4 were highly stereospecifically synthesized over 4-6 steps from commercially available starting materials. The coupling reaction of the acetobromo-α-D-glucose with the unprotective dihydroxy aglycon in the presence of silver oxide, or with aromatic aglycon in the presence of sodium hydroxide produced the key intermediate. Only β-configuration glycosides were formed in this procedure. The synthesis of all these glycosides was reported for the first time.Alkyl glucoside 1 and aryl glycosides 2-4 were highly stereospecifically synthesized over 4-6 steps from commercially available starting materials. The coupling reaction of the acetobromo-α-D-glucose with the unprotective dihydroxy aglycon in the presence of silver oxide, or with aromatic aglycon in the presence of sodium hydroxide produced the key intermediate. Only β-configuration glycosides were formed in this procedure. The synthesis of all these glycosides was reported for the first time.

关 键 词：stereospecifical synthesis aryl β-D-glucopyranoside coupling reaction 

分 类 号：O629.1[理学—有机化学]