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Synthesis 2002(4): 0487-0490
DOI: 10.1055/s-2002-20962
PAPER
© Georg Thieme Verlag Stuttgart · New York

Optimized Synthesis of an Orthogonally Protected Glucosamine

Jesús M. Hernández-Torres, Siong-Tern Liew, Jihane Achkar, Alexander Wei*
Department of Chemistry, Purdue University, 1393 Brown Building, West Lafayette, Indiana 47907-1393, USA
Fax: +1(765)4940239; e-Mail: alexwei@purdue.edu;
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Publication History

Received 1 September 2001
Publication Date:
28 July 2004 (online)

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Abstract

Glucosamine hydrochloride was transformed into an orthogonally protected intermediate in seven steps and 34% over­all yield. The synthesis includes an optimized preparation of N-phthaloyl-β-d-glucosamine tetraacetate, a commonly used precursor in carbohydrate chemistry.

Keywords

carbohydrates - glucosamine - glycosides - orthogonal protecting groups

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Wong and co-workers have reported that the corresponding p-tolyl thioglycoside could be recrystallized straight forwardly from EtOH. [12]