Method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanoli

Details Method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanoli Method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanoli

1993-07-23

1995-05-02

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30733

Patent

active

054121116

ABSTRACT:
Providing a method of preparing (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanolide conveniently and selectively from a widely available raw material in a high yield. A carbonyl group of the 2-position of levoglucosenone is reduced to obtain a hydroxyl group of a .beta.-configuration. Then, an iodo-group of an .alpha.-configuration and an acyloxy ion of a .beta.-configuration are introduced regioselectively and stereoselectively to the double bond at the 4-position and the 3-position of the above-mentioned levoglucosenone, respectively, keeping a trans stereochemical relationship. An alkoxide is then formed, by hydrolysis and an oxirane ring of a .beta.-configuration is formed by removing an iodo-group by intramolecular nucleophilic displacement reaction of the alkoxide. After the hydroxyl group of the 2-position is oxidized to convert to a carbonyl group, the oxirane ring is reductively and selectively cleaved, thereby obtaining a chemical compound having no substituent at the 3-position and a hydroxyl group of a .beta.-configuration at the 4-position. Finally a lactone of 5-membered-ring is prepared by subjecting the above-obtained compound to Baeyer-Villigar oxidation.

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