Phosphonic Acid Analogs of Carbohydrate Metabolites. IV. Synthesis of DL-Glyceraldehyde-3-phosphonic Acid

A chemical synthesis of DL -glyceraldehyde-3-phosphonic acid, the phosphonic acid analog of DL -glyceraldehyde-3-phosphoric acid, is reported. It was obtained from dimer DL -glyceraldehyde by two procedures differing solely in their protective groups via the following intermediates. Procedure 1: 2,5...

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Bibliographic Details
Published in:Canadian journal of chemistry 1973-01, Vol.51 (1), p.104-110
Main Authors: Baer, Erich, Robinson, Ranga
Format: Article
Language:English
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Summary:A chemical synthesis of DL -glyceraldehyde-3-phosphonic acid, the phosphonic acid analog of DL -glyceraldehyde-3-phosphoric acid, is reported. It was obtained from dimer DL -glyceraldehyde by two procedures differing solely in their protective groups via the following intermediates. Procedure 1: 2,5-diiodomethyl-3,6-dimethoxy-1,4-dioxane → 2,5-bis(methylphosphonic acid diethyl ester)-3,6-dimethoxy-1,4-dioxane → 2,5-bis(methylphosphonic acid)-3,6-dimethoxy-1,4-dioxane → DL -glyceraldehyde-3-phosphonic acid. Procedure 2: 2,5-bis(p-toluenesulfonyloxymethyl)-3,6-dibenzoxy-l,4-dioxane → 2,5-diiodomethyl-3,6-dibenzoxy-l,4-dioxane → 2,5-bis(methylphosphonic acid diethyl ester)-3,6-dibenzoxy-l,4-dioxane → 2,5-bis(methylphosphonicacid)-3,6-dibenzoxy-1,4-dioxane → DL -glyceraldehyde-3-phosphonic acid.
ISSN:0008-4042
1480-3291
DOI:10.1139/v73-015