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 corresponding deoxy sugars. In spite of some improvements in the preparation of 2, the optical yield of this step was only ∼80%, but one crystallisation from chloroform raised the optical purity to 96%. The subsequent steps produced a loss in optical purity of only 4%.
|Autori:||BERTI G; CAROTI P; CATELANI G; FARINA C; MONTI L|
|Titolo:||SYNTHESIS OF D-AMICETOSE AND L-RHODINOSE FROM L-GLUTAMIC ACID|
|Anno del prodotto:||1983|
|Digital Object Identifier (DOI):||10.1016/0008-6215(83)88353-0|
|Appare nelle tipologie:||1.1 Articolo in rivista|