Chin. J. Org. Chem. ›› 1997, Vol. 17 ›› Issue (1): 38-42. Previous Articles     Next Articles

Original Articles

1,2和1,3-缩水内醚糖衍生物的制备, 构象及其糖苷化反应

孔繁祚   

  1. 中国科学院生态环境研究中心
  • 发布日期:1997-02-25

Synthesis, conformation, and glycosidic coupling reaction of 1,2- and 1,3-anhydro sugar derivatives

KONG FANZUO   

  • Published:1997-02-25

The synthesis of 1,2- and 1,3-anhydro glycopyranose benzyl ethers ws successfully achieved via intramolecular SN2 reaction of the corresponding C-2 (or C-3 for 1,3-anhydro sugars) alkoxide with C-1 bearing chloride, and the synthesis of some 1,2-anhydro pyranoses by the intramolecular reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group (inverse ring closure). The synthesis of 1,2-anhydro glycofuranose benzyl ethers was carried out only by the inverse ring closure. Ring opening of the 1,2- and 1,3-anhydro sugars usually afforded 1,2-trans and 1,3-trans linked glycosides respectively. Conformational analysis of the 1,2- and 1,3-anhydro sugars was performed by ^1H NMR spectrometry and molecular mechanics calculations.

Key words: PROTON MAGNETIC RESONANCE SPECTROMETRY, CONFORMATION, FURANOSE, PYRANOSE

CLC Number: