THE C- AND O-BENZYLATION OF L-ASCORBIC ACID
- 1 February 1965
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 43 (2), 450-457
- https://doi.org/10.1139/v65-060
Abstract
Alkylation of sodium L-ascorbate with benzyl chloride yielded a 2-C-benzyl-3-keto-hexulosonic acid lactone and 3-O-benzyl-L-ascorbic acid, the yield of each being dependent on reaction conditions. Other products obtained from the alkylations were 2,3-di-O-benzyl-L-ascorbic acid and a 1-deoxy-1-C-phenyl-2-hexulose. Treatment of 3-O-methyl-5,6-O-isopropylidene-L-ascorbic acid with benzyl chloride and sodium methoxide yielded the 2-O-benzyl derivative.This publication has 10 references indexed in Scilit:
- Isomerization of the Ascorbic AcidsThe Journal of Organic Chemistry, 1964
- Heterogeneity as a Factor in the Alkylation of Ambident Anions: Phenoxide Ions1,2Journal of the American Chemical Society, 1959
- Formation of Cyclohexadienones by Direct Alkylation of Phenols with Saturated Alkyl Derivatives1Journal of the American Chemical Society, 1958
- Factors Controlling Position of Alkylation of Alkali Metal Salts of Phenols, Benzyl and Allyl Halides1,2Journal of the American Chemical Society, 1958
- The Synthesis of 3-Hexuloses. Part 1. 2-O-Methyl-L-xylo-3-hexulose1Journal of the American Chemical Society, 1956
- Quantitative Bestimmung reduzierender Zucker durch Papierchromatographie sowie eine Anwendung zur Mikrobestimmung der BlutzuckerAngewandte Chemie, 1953
- The estimation of small amounts of formaldehyde liberated during the oxidation of carbohydrates and other substances with periodateBiochemical Journal, 1953
- Detection of Sugars on Paper ChromatogramsNature, 1950
- BIOCHEMICAL INDIVIDUALITY .4. A PAPER CHROMATOGRAPHIC TECHNIQUE FOR DETERMINING EXCRETION OF AMINO ACIDS IN THE PRESENCE OF INTERFERING SUBSTANCES1949
- THE ROTATORY POWERS OF THE AMIDES OF ACTIVE α-HYDROXY ACIDS.Journal of the American Chemical Society, 1918