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Synthesis of chiral 4-pyrazolol derivatives starting from D-glucose

✍ Scribed by D. de Wit; L. M. A. van Unen; F. van Rantwijk; L. Maat; A. P. G. Kieboom

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
416 KB
Volume
111
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

The condensation of protected and unprotected 3‐ketoglucose (1) with hydrazines to 4‐pyrazolols has been investigated. 3‐ (5) and 5‐(D‐erythro‐1,2,3‐trihydroxypropyl)‐4‐pyrazolol (4) were obtained from 1 in high yield, as a mixture of these two isomers. A regioselective route starting from protected 1 in two steps yielded a mixture of diastereomers as a result of epimerization in the side chain.

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