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

Article abstract of DOI:10.1002/recl.19921111003

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.