Preparation of Per-O-acetylated (S)-TBMB Carboxylic Acid Derivant of Methyl-4-amino-4-deoxy-D-glucopyranoside

Abstract

Abstract: Starting from D-galactose, per-O-acetylated (S)-TBMBcarboxylic acid derivant of methyl-4-amino-4-deoxy-D-glucopyranoside was prepared. The mechanism of the possible side reactions of the catalytic reduction from different types of azide sugar to the corresponding amino sugar was discussed. 1-O-Me-protection was selected for preventing the intramolecular dehydration of the 4-amino sugar, which was a key intermediate product in this synthetic process. The product was characterized by HRMS and ¹H NMR spectroscopy and will be used as a molecular model to develop a new identification method of the D, L-configurations of amino sugar.

Key words: Azido sugar, Catalytic reduction, Methyl-4-amino-4-deoxy-D-glucopyranoside

CLC Number:

Q532

TrendMD:

BAI Chen, LIANG Bo, WANG Shu-Zhen, ZHENG Xiao-Xun. Preparation of Per-O-acetylated (S)-TBMB Carboxylic Acid Derivant of Methyl-4-amino-4-deoxy-D-glucopyranoside[J]. Chem. J. Chinese Universities, 2002, 23(9): 1724.

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Preparation of Per-O-acetylated (S)-TBMB Carboxylic Acid Derivant of Methyl-4-amino-4-deoxy-D-glucopyranoside

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