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Enantiospecific syntheses of 3,4-dideoxy-oct-2-ulosonic acids

✍ Scribed by Tony K.M. Shing

Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 805 KB
Volume: 48
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89867-7

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✦ Synopsis

Ethyl 5,6,7,8-tetra-Oacetyl-3,4-dideoxy-D-arabiflPoct-2-ulosonate and ethyl 3,4dideoxy-5.6:7,8-di-Oisopropylidene-D-afaM?o-oct-2-ulosonate have been synthesised from peracetylated and bisacetonated Mehydo-Darabinose respectively by a two stage procedure: Wittig reaction and catalytic hydrogenation. Deprotecfion of the blocked ethyl act-Pubsonate afforded the 3,4dldeoxy-D-afa&?ind-oct-2-ulosonic acid (Cdeoxy-KDO), isolated as lts calcium salt in an overall yield of 37% from D-arabinose. Likewise reactions of D-xylose gave calcium 3,4dideoxy-Dxylo-act-Pulosonate

in an overall yield of 34%. Both calcium salts were derivatised as crystalline quinoxaline tetraacetates. Other routes attempted are also described.

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