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New syntheses of d- and l-glycero-d-manno-heptoses

✍ Scribed by Krzysztof Dziewiszek; Aleksander Zamojski

Publisher: Elsevier Science
Year: 1986
Tongue: English
Weight: 607 KB
Volume: 150
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(86)80013-1

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✦ Synopsis

Three methods for the synthesis of the title compounds starting from benzyl 2,3,4-tri-O-benzyl-cr-D-manno-hexodialdo-1,5-pyranoside (7) have been elaborated. Conversion of 7 into the cyanohydrin followed by reduction to give the amine and then deamination gave a derivative of L-glycero-D-manno-heptose in low yield. Condensation of 7 with 2methylfuran gave two stereoisomeric 6-C-(2methyl-5furyl) derivatives. The preponderant stereoisomer was ozonised and then reduced to give a derivative of D-glycero-D-munno-heptose. Condensation of 7 with allyloxymethylmagnesium chloride gave derivatives of both heptoses in good yield and with an L-glyceru-mglycero ratio of 3.2:1. Deprotection of these derivatives gave the heptoses in high yield.

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