Carbohydrate research

Synthesis of D-amicetose and L-rhodinose from L-glutamic acid

G Berti, P Caroti, G Catelani, L Monti

Index: Berti, Giancarlo; Caroti, Paola; Catelani, Giorgio; Monti, Luigi Carbohydrate Research, 1983 , vol. 124, p. 35 - 42

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Citation Number: 24

Abstract

Abstract l-Glutamic acid has been converted into a separable mixture of d-amicetono-and l- rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ- butyrolactone (2), conversion of 2, conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or borane-methyl sulfide. Reduction of the two lactones with di-isobutylaluminium hydride gave the ...