2,3,6,3′,4′-五氧乙酰基蔗糖的合成与表征

The Synthesis and Structure Characterization of 2,3,6,3′, 4′-Penta-oxyacetylsucrose

以蔗糖为原料通过羟基的选择性保护、脱保护及迁移合成了三氯蔗糖的中间体2,3,6,3′,4′-五氧乙酰基蔗糖(6-PAS)。在蔗糖羟基的选择性保护反应中采用4-二甲氨基吡啶(DMAP)为催化剂,有效地提高了产率,并利用HPLC对选择性脱保护和乙酰基迁移2步反应进行跟踪,确定了较优的合成路线。并用核磁共振和红外光谱对产品进行表征。羟基选择性保护最佳反应条件为:使用质量分数为10％的催化剂,三苯甲基化反应在50℃进行4 h,乙酰化反应在105℃进行3 h。在该条件下进行反应,产率为81．9％。

2,3,6,3＇ ,4＇-Penta-O-acetylsucrose（6-PAS） was synthesized from sucrose via tritylation, acetylation, detritylation and acetyl migration. An effective reagent protecting the hydroxyls of sucrose was used to improve the yield of the reaction. In the process of protecting, the effects of reaction temperature and reaction time were studied. The two steps of detritylation and acetyl migration were analyzed by HPLC to chose the better route. The products were characterized by means of ^1 H NMR and IR. The result shows that the optimum conditions for protecting hydroxyl are ： tritylation at 50 ℃ for 4 h and acetylation at 105 ℃ for 3 h. The yield is 81.9%.