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有机化学
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有机化学 ›› 2001, Vol. 21 ›› Issue (3): 214-217. 上一篇    下一篇

研究论文

糖基亚苄基NaBH3CN-HCl选择性开环过程中乙酰基迁移 现象的研究

秦致辉;蔡孟深;李中军   

  1. 北京医科大学药学院生物有机系;天然药物与仿生药物国家重点实验室
  • 发布日期:2001-03-25

Studies on the migration of acetyl group during the process of reductive ring-opening of 4,6-O-benzylidene thioglycoside with NaBH3CN-HCl

Qin Zhihui;Cai Mengshen;Li Zhongjun   

  • Published:2001-03-25

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被引次数

1

用NaBH3CN-HCl/Et2O对3-O-乙酰基-4，6-O-亚苄基-β-D-吡喃半乳糖乙硫苷(2)进行还原开环，发现有乙酰基迁移至2-位的产物生成；进一步的实验表明，室温条件下，NaBH3CN与2的作用导致乙酰基的迁移。

关键词: 反应机理, 硼氢化作用, 半乳糖, 巯基, 糖化学, 吡喃糖, 糖苷, 开环反应, 选择还原, 乙酰基, 迁移

Reductive opening of the 4,6-O-benzylidene ring of ethyl 3-O-acetyl- 4,6-O-benzyli-dene-β -D-galactopyranothioglycoside (2) with NaBH3CN- HCl/Et2O gave an unexpected product with the acetyl group migrated to the 2-OH. Further experiment showed that the migration was induced by NaBH3CN at room temperature.

Key words: REACTION MECHANISM, HYDROBORATION, GALACTOSE, MERCAPTO GROUP, PYRANOSE, GLYCOSIDE, RING CLEAVAGE REACTION, SELECTIVE REDUCTION, ACETYL GROUP, MIGRATION

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