Vitamin‐C‐ and isovitamin‐C‐derived chemistry. Part I. Synthesis of 2,3‐dideoxy derivatives of the Ascorbic acids
Author(s) -
Vekemans Jozef A. J. M.,
Boerekamp Jack,
Godefroi Erik F.,
Chittenden Gordon J. F.
Publication year - 1985
Publication title -
recueil des travaux chimiques des pays‐bas
Language(s) - English
Resource type - Journals
ISSN - 0165-0513
DOI - 10.1002/recl.19851041005
Subject(s) - chemistry , dimethylformamide , ascorbic acid , acetal , methanol , dioxolane , enantiomer , chloroform , organic chemistry , thermal decomposition , decomposition , vitamin , vitamin c , biochemistry , food science , solvent
5,6‐ O ‐Isopropylidene‐L‐gulono‐ and ‐D‐mannono‐1,4‐lactones are converted into 2‐(dimethylamino)‐1,3‐dioxolane derivatives on treatment with N,N ‐dimethylformamide dimethyl acetal in chloroform with azeotropic removal of the methanol thus formed. Quaternisation of the products with iodomethane, followed by thermal decomposition yields the corresponding C(4)‐substituted enantiomeric butenolides. Some aspects of the reactions, the characterisation of the products, and further transformations are described.
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