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A synthesis in one reaction vessel of 2,4-diamino sugar precursors from 2,3-dideoxy-2-enopyranos-4-uloses

✍ Scribed by Elias A. Couladouros; Violetta Constantinou-Kokotou; Minas P. Georgiadis; George Kokotos

Book ID
102998479
Publisher
Elsevier Science
Year
1994
Tongue
English
Weight
530 KB
Volume
254
Category
Article
ISSN
0008-6215

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✦ Synopsis

2,CDiaminosugars are components of several natural products, especially antibiotics such as kasugamycin', prumycin*, and minosaminomycin3. Since their discovery a great number of analogues have been synthesized4. Amongst them, deoxygenated derivatives that lack centers for detoxification have shown improved antibiotic properties5.

Our synthetic interest in aminodeoxy sugars w has stimulated us to develop a simple and general method for the synthesis of racemic, N-protected 2,4-diamino-2,3,4,-trideoxypentapyranosides.

The 2,3-dideoxy-2-enopyranos-4-uloses l-3 (ref 8) were the starting materials for our procedure, since they possess the carbohydrate skeleton, as well as a Michael center and a carbonyl function, which are the ideal entry points for the introduction of the amino functionalities.

* This paper is no. 24 in the series Products from Furans. For previous papers, see ref 8.

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