蔗糖分子中羟基的选择性保护的研究

蔗糖和原乙酸三烷基酯反应后,经三苯甲基化、乙酰化以及乙酰基由4-位到6-位的基团迁移反应,选择性地保护了蔗糖分子中的羟基基团,合成了一系列蔗糖乙酸酯.4,6-原乙酸蔗糖六乙酸酯在酸催化下水解和醇解,相应地得到2,3,6,1',3',4',6'-七-O-乙酰基蔗糖和2,3,1',3',4',6'-六-O-乙酰基蔗糖。这些都是合成蔗糖衍生物方便的中间体,在糖化学的研究中得到应用.

Studies on the Selectively Protecting Groups of Hydroxyls in Sucrose

Reaction of sucrose with trialkyl orthoacetate,subsequent tritylation,acetylation,and detritylation afforded derivatives of sucrose acetate by selectively blocking specific hydroxyls in sucrose and 4-6 acetyl migration.The treatment of sucrose alkyl 4,6-orthoacetate hexaaeetate with water or alcohol in the presence of an acid catalyst afforded corresponding 2,3,6,1',3',4',6'-hepta-O-acetylsucrose and 2,3.1',3',4',6'-hexa-O-acetylsucrose.These derivatives of sucrose acetate were available from sucrochemical studies and have been developed as convenient intermediate for the synthesis of sucrose derivatives.