Total Syntheses of Carbohydrates. I. Dihydroxyacetone and Dl-Erythrulose
- 1 August 1972
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 45 (8) , 2611-2615
- https://doi.org/10.1246/bcsj.45.2611
Abstract
An improved method of preparation of halopropargyl alcohol is described. Hydration of halopropargyl alcohol followed by hydrolysis gave dihydroxyacetone which was identified as its dibenzoate. 2-Butyne-1,4-diol was converted into acetoxymethyl vinyl ketone. 1,4-Diacetoxy-3-bromobutan-2-one obtained by the addition of acetyl hypobromite to the vinyl ketone was treated with silver acetate to yield tri-O-acetyl-Dl-erythrulose. Hydrolysis of the triacetate afforded Dl-erythrulose which was identified as phenylhydrazone.This publication has 21 references indexed in Scilit:
- Studies on Acetylenic Compounds. XXXVI. Total Synthesis of Ethyl 3-Amino-3-deoxy-β-DL-arabinofuranoside.CHEMICAL & PHARMACEUTICAL BULLETIN, 1963
- Studies on Acetylenic Compounds. XXIX. A New Method for Synthesis of DL-Ribose.CHEMICAL & PHARMACEUTICAL BULLETIN, 1963
- Studies on Acetylenic Compounds. XXVIII. A Synthesis of DL-Arabinose and DL-Ribose.CHEMICAL & PHARMACEUTICAL BULLETIN, 1963
- The synthesis of L-()-mycarose and L-()-cladinoseTetrahedron, 1962
- Studies on Acetylenic Compounds. XVII. Total Synthesis of dl-Ribose and dl-Arabinose.CHEMICAL & PHARMACEUTICAL BULLETIN, 1961
- Studies on Acetylenic Compounds. XVIII. Total Synthesis of dl-Lyxose and dl-Xylose.CHEMICAL & PHARMACEUTICAL BULLETIN, 1961
- Karlsruher Chemische GesellschaftAngewandte Chemie, 1957
- 2‐Desoxy‐DL‐ribose und 2‐Desoxy‐DL‐xylose aus 1‐Methoxy‐ buten‐(1)‐in‐(3)European Journal of Inorganic Chemistry, 1956
- Zur Kenntnis des DioxyacetonsMonatshefte für Chemie / Chemical Monthly, 1951
- Derivatives of the oxidation products of glycerolRecueil des Travaux Chimiques des Pays-Bas, 1937