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

Tony K.M. Shing

doi:10.1016/S0040-4039(00)91608-3

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

Tony K.M. Shing

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

Bisacetonated aldehydo-d-arabinose has been converted by three consecutive reactions (Wittig reaction, catalytic hydrogenation, and hydrolysis) into 3,4-dideoxy-d-arabino-oct-2-ulosonic acid (4-deoxy-KDO), isolated as its calcium salt in an overall yield of 37% from d-arabinose. Likewise reactions of d-xylose gave calcium 3,4-dideoxy-d-xylo-oct-2-ulosonate in an overall yield of 34%.

Original language	English
Pages (from-to)	1307-1308
Number of pages	2
Journal	Tetrahedron Letters
Volume	33
Issue number	10
DOIs	https://doi.org/10.1016/S0040-4039(00)91608-3
Publication status	Published - 1992 Mar 3

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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abstract = "Bisacetonated aldehydo-d-arabinose has been converted by three consecutive reactions (Wittig reaction, catalytic hydrogenation, and hydrolysis) into 3,4-dideoxy-d-arabino-oct-2-ulosonic acid (4-deoxy-KDO), isolated as its calcium salt in an overall yield of 37% from d-arabinose. Likewise reactions of d-xylose gave calcium 3,4-dideoxy-d-xylo-oct-2-ulosonate in an overall yield of 34%.",

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N2 - Bisacetonated aldehydo-d-arabinose has been converted by three consecutive reactions (Wittig reaction, catalytic hydrogenation, and hydrolysis) into 3,4-dideoxy-d-arabino-oct-2-ulosonic acid (4-deoxy-KDO), isolated as its calcium salt in an overall yield of 37% from d-arabinose. Likewise reactions of d-xylose gave calcium 3,4-dideoxy-d-xylo-oct-2-ulosonate in an overall yield of 34%.

AB - Bisacetonated aldehydo-d-arabinose has been converted by three consecutive reactions (Wittig reaction, catalytic hydrogenation, and hydrolysis) into 3,4-dideoxy-d-arabino-oct-2-ulosonic acid (4-deoxy-KDO), isolated as its calcium salt in an overall yield of 37% from d-arabinose. Likewise reactions of d-xylose gave calcium 3,4-dideoxy-d-xylo-oct-2-ulosonate in an overall yield of 34%.

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JO - Tetrahedron Letters

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

Abstract

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