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Synthesis 2009(16): 2756-2760  
DOI: 10.1055/s-0029-1217605
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© Georg Thieme Verlag Stuttgart ˙ New York

Stereocontrolled Formation of Protected Aminodeoxyalditols from Simple Carbohydrate Precursors by Debenzylating Cycloetherification

Yuhua Jiang, Zhijie Fang*, Qiangang Zheng, Hailang Jia, Jie Cheng, Baohui Zheng
School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, P. R. of China
Fax: +86(25)84314906; e-Mail: zjfang@mail.njust.edu.cn;
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Publication History

Received 3 March 2009
Publication Date:
10 July 2009 (online)

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Abstract

A new and highly efficient methodology for the stereocontrolled synthesis of aminodeoxyalditols is described through a dimesylation/intramolecular SN2 nucleophilic substitution ring-forming reaction sequence from glucose, mannose, and galactose derivatives. The degree of difficulty and rate of the reaction of dimesylates in the cyclization process is evaluated and shows the trend: galactose > glucose > mannose derivatives, which has been identified from our experiments and classical theories.

Key words

intramolecular cyclization - debenzylation - anhydrosugar - azido group - stereocontrolled synthesis