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Use of Glucosyl 3,5-Dinitrobenzoate in Synthesis of Glucosides and Related Oligosaccharides

HUANG He-qing, LI Qing, CAI Meng-shen, LI Zhong-jun*   

  1. 1.Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100083, China;
    2.Department of Chemistry, Xinxiang Medical College, Xinxiang 453003, China
  • Received:2004-06-10 Revised:2004-11-10 Online:2004-12-15 Published:2004-12-15
  • Contact: LI Zhong-jun*

Abstract: Aim To investigate a new glycosylation method. Methods In the presence of TMSOTf as catalyst, 1-O-(3, 5-dinitrobenzoyl)-2, 3, 4, 6-tetra-O-benzyl-α-D-glucopyranose 1 reacted with a series of carboxylic acid, phenols, alcohols and saccharides respectively to give the corresponding glycosylation products. The compounds were determined by 1H NMR and 13C NMR spectra. Results The α-gluco-pyranosides and related oligosaccharides were prepared in high yields. Conclusion The 3, 5-dinitrobenzoyl group was found to be a good leaving group at the anomeric position and O-glucopyranosides and oligosaccharides were stereoselectively synthesized in good yield.

Key words: glucosyl 3,5-dinitrobenzoate, glucosyl 3,5-dinitrobenzoate, glycosylation, glycosylation, stereoselectivity, stereoselectivity

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