TY - JOUR
T1 - Vitamin-C- and isovitamin-C-derived chemistry, Part I. : synthesis of 2,3-dideoxy derivatives of the ascorbic acids
AU - Vekemans, J.A.J.M.
AU - Boerekamp, J.G.
AU - Godefroi, E.F.
AU - Chittenden, G.J.F.
PY - 1985
Y1 - 1985
N2 - 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.
AB - 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.
U2 - 10.1002/recl.19851041005
DO - 10.1002/recl.19851041005
M3 - Article
SN - 0165-0513
VL - 104
SP - 266
EP - 272
JO - Recueil des Travaux Chimiques des Pays-Bas
JF - Recueil des Travaux Chimiques des Pays-Bas
IS - 10
ER -