Chin. J. Org. Chem. ›› 2001, Vol. 21 ›› Issue (3): 214-217. Previous Articles     Next Articles

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

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

CLC Number: