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有机化学
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有机化学 ›› 2002, Vol. 22 ›› Issue (2): 127-129. 上一篇    下一篇

研究论文

碘/甲醇体系对甘油醚脱保护

许新华;陈茹玉   

  1. 湖南大学化学化工学院,长沙(410081);南开大学元素有机化学研究所.天津 (300071)
  • 发布日期:2002-02-25

Deprotection of glycerol ether using iodine-methanol

Xu Xinhua;Chen Ruyu   

  1. College of Chemistry and Chemical Engineering, Hunan University, Changsha(410082);Institute of Elemento-Orgemistry, Nankai University. Tianjin(300071)
  • Published:2002-02-25

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被引次数

12 | 4

1-烷氧基-2乙酰氧基-3-三苯甲氧基甘油醚与碘/甲醇体系反应，在60 ℃时， 同时发生了脱三苯甲基及乙酰基，在室温下，仅脱三苯甲基，但乙酰基在反应过程 中发生了部分转移，产生了两个异构体。碘/甲醇体系与1-烷氧基-2，3-异丙叉甘 油醚反应，高收率地生成1-烷氧基甘油。脱保护机理是一个酸催化过程，据此提出 并证实了碘水四氧呋喃体系同样能进行上述脱保护反应。

关键词: 去保护, 缩水甘油醚, 碘, 甲醇, 四氢呋喃

At 60 ℃ the reaction of 1-O-alkyl-2-O-acetyl-3-O-trityl glycerol with iodine/methanol system removed trityl and acetyl and gave 1-alkyl glycerol. But at r.t. the reaction only removed trityl and gave two isomers 1-O-alkyl-2-O-acetyl glycerol and 1-O-alkyl-3-O-acetyl glycerol. 1-O-Alkyl-2,3-O, O-propylidene glycerol reacted with iodine/methanol system to give 1-O-alkyl glycerol in high yields. The reaction is belived to have an acid-catalyzed mechanism. Iodine/water/THF system could also be used for the deprotection.

Key words: deprotection, GLYCIDYL ETHER, IODINE, METHANOL, TETRAHYDROFURAN

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