氧化银(Ⅰ)在糖羟基上选择性对-甲基苯磺酰化中的应用  

Highly Selective p-Monotosylation of Hydroxyls of Saccharide in the Presence of Ag_2O

作　　者：佘戟[1] 

机构地区：[1]广东医学院化学教研室,湛江524023

出　　处：《应用化学》2005年第2期230-232,共3页Chinese Journal of Applied Chemistry

摘　　要：Silver（Ⅰ） oxide was applied to the selective p-tosylation of hydroxyls of saccharide. The reaction of p-methylphenyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside（A） with a stoichiometric amount of p-toluenesulfonyl chloride（TsCl） in the presence of silver（Ⅰ） oxide and a catalytic amount of potassium iodide selectively led to the monotosylate derivative:p-methylphenyl 3-O-p-toluenesulfonyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside（B） in a high yield（97%）. A possible mechanism of the reaction is proposed. The rational reaction process is that at n（TsCl）∶n（Ag2O）∶n（A）∶n（KI）=1.2∶1.5∶1.0∶0.2, the mixture is stirred at room temperature for 8 h, 2.74 g（97%）B could be isolated from 2.0 g of compound A.Silver(Ⅰ) oxide was applied to the selective p-tosylation of hydroxyls of saccharide. The reaction of p-methylphenyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside(A) with a stoichiometric amount of p-toluenesulfonyl chloride(TsCl) in the presence of silver(Ⅰ) oxide and a catalytic amount of potassium iodide selectively led to the monotosylate derivative:p-methylphenyl 3-O-p-toluenesulfonyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside(B) in a high yield(97%). A possible mechanism of the reaction is proposed. The rational reaction process is that at n(TsCl)∶n(Ag_2O)∶n(A)∶n(KI)=1.2∶1.5∶1.0∶0.2, the mixture is stirred at room temperature for 8 h, 2.74 g(97%)B could be isolated from 2.0 g of compound A.

关 键 词：氧化银(Ⅰ) 选择性对-甲基苯磺酰化 糖羟基 

分 类 号：O621[理学—有机化学]