The syntheses of 4,6-dideoxy-4,6-difluoro- and 4-deoxy-4-fluoro-α,α-trehalose

作     者：Hadfield, Anthony F. Hough, Leslie Richardson, Anthony C. 

作者机构：Department of Chemistry Queen Elizabeth College (University of London) London W8 7AH Campden Hill Road United Kingdom 

出 版 物：《Carbohydrate Research》 (Carbohydr. Res.)

年 卷 期：1979年第71卷第1期

页      面：95-102页

学科分类：0710[理学-生物学] 081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

摘      要：Prolonged treatment of 2,3-di-O-benzyl-4,6-di-O-mesyl-α-d-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-d-glucopyranoside with tetrabutylammonium fluoride in acetonitrile gave the 4,6-difluoride (71 % yield), from which 4,6-dideoxy-4,6-difluoro-α-d-galactopyranosyl α-d-glucopyranoside was prepared. In a similar reaction with 2,3-di-O-benzyl-4,6-di-O-mesyl-α-d-galactopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-d-glucopyranoside, two products were formed, as indicated by the 19F-n.m.r. spectrum of the reaction mixture, and tentatively identified as the required 4,6-difluoride and the 6-fluoro-4-ene. Fluoride displacement of the mesyloxy group of 2,3-di-O-benzyl-4-O-mesyl-6-O-trityl-α-d-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-d-glucopyranoside readily gave the 4-fluoride which, on deprotection, gave 4-deoxy-4-fluoro-α-d-galactopyranosyl α-d-glucopyranoside. © 1979.