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应用苯甲醇钠裂解氧三圜型内醚醣醚环的研究

A Study of the Scission of Ethylene Oxide Ring in α-Methyl 2:3-Anhydro-4:6-benzylidene-D-allopyranoside by Sodium Benzylate

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【作者】 张滂李思固

【Author】 Pang Chang Peking University,Peking Basil Lythgoe Cambridge University,England

【机构】 北京北京大学英国剑桥大学

【摘要】 应用苯甲醇钠可以裂解α-甲基2∶3-内醚-4∶6-苯亚甲基-D-同侧醣氧六圜配醣物的醚环,生成53%的α-甲基2-苯甲基-4∶6-苯亚甲基-D-2-异侧醣氧六圜配醣物及9%的α-甲基3-苯甲基-4∶6-苯亚甲基-D-葡萄糖氧六圜配醣物。此两化合物的结构,应用水解除去苯亚甲基及接触氢解除去苯甲基后,证明是已知的α-甲基 D-2-异侧醣氧六圜配醣物,及α-甲基 D-葡萄糖氧六圜配醣物;苯甲基在醣分子中的衔接位置,则应用高碘酸钠氧化测定。

【Abstract】 The anhydro ring in a-methyl 2:3-anhydro-4:6-benzylidene-D-allopyranosidehas been opened by the action of sodium benzylate to give 53% yield ofα-methyl 2-benzyl-4:6-benzylidene-D-altropyranoside and 9% of a-methyl 3-benzyl-4:6-benzylidene-D-glucopyranoside.After the removal of the benzy-lidene residue by acid hydrolysis,the position of attachment of the benzylgroup is determined by periodate oxidation.Catalytic hydrogenolysis of thebenzyl group gives the known α-methyl D-altroside and a-methyl D-glucosiderespectively and their constitutions are thus proved.While an ethylene oxide ring in a sugar molecule can be opened by alkaline reagents,such as sodium hydroxide,sodium methoxide,ammonia,etc,the use of sodium benzylate has the advantage that one of the hydroxylgroups is protected after the scission by the benzyl group which can in turnbe removed by catalytic hydrogenation.

  • 【文献出处】 化学学报 ,Acta Chimica Sinica , 编辑部邮箱 ,1953年02期
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