A Facile and Stereoselective Synthesis of 3,4,6-Tri-O-Acetyl-2-Deoxy-2-Phthalimido-β-D-Glucopyranosyl Chloride-Reference-Cited by-同舟云学术

A Facile and Stereoselective Synthesis of 3,4,6-Tri-O-Acetyl-2-Deoxy-2-Phthalimido-β-D-Glucopyranosyl Chloride

Published:2013-08 Issue:8 Volume:37 Page:467-469
ISSN:1747-5198
Container-title:Journal of Chemical Research
language:en
Short-container-title:Journal of Chemical Research

Author:

Cao Zhiling¹²,Liu Wenjie¹,Qu Yingying¹,Yao Guowei³,Gao Dachao¹,Liu Weiwei¹

Affiliation:

1. Jiangsu Key Laboratory of Marine Biotechnology, Huaihai Institute of Technology, Lianyungang 222005, P. R. China

2. Jiangsu Marine Resources Development Research Institute, Lianyungang 222001, P. R. China

3. School of Life Science, Beijing Institute of Technology, Beijing 100081, P. R. China

Abstract

Acetylation of D-glucosamine catalysed by sulfuric acid and N-phthaloylation of the glucosyl acetate yielded 1,3,4,6-tetra- O-acetyl-2-deoxy-2-phthalimido-α-D-glucopyranose. This gave the corresponding pure β-glucosyl chloride upon treatment with PCl5-BF3. An anomeric chlorination with thionyl chloride combined with the Lewis acids (ZnCl2, SnCl4 and BiCl3) resulted in an α/β anomer mixture.

Publisher

SAGE Publications

Subject

General Chemistry

Link

http://journals.sagepub.com/doi/pdf/10.3184/174751913X13728407114482

Reference26 articles.

1. Synthesis of Glycopeptides Containing Carbohydrate and Peptide Recognition Motifs

2. Molecular Insights into Aminoglycoside Action and Resistance

3. Glycosyl Sulfonium Ions as Storable Intermediates for Glycosylations

4. Recent trends in the synthesis of O-glycosides of 2-amino-2-deoxysugars

5. Chemical Synthesis of CD52 Glycopeptides Containing the Acid-Labile Fucosyl Linkage

Cited by 1 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Glycosidic bond formation methodology: challenges and impact in oligosaccharide synthesis;Synthetic Strategies in Carbohydrate Chemistry;2024