Organic compounds -- part of the class 532-570 series – Organic compounds – Fatty compounds having an acid moiety which contains the...
Patent
1994-10-04
1996-06-11
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Fatty compounds having an acid moiety which contains the...
554 63, 554108, 554109, 554110, C07C25100
Patent
active
055257097
ABSTRACT:
The invention relates to the preparation of ceramides by a two step process involving conversion of a 2-hydroximino-3-oxo-alkanoate into a 2-alkanoylamido-3-oxo-alkanoate intermediate by acylation of the oxime and reduction of the oxime ester group to an amido group, followed by reduction of the keto and ester group of the intermediate to the 1,3 diol of the ceramide. The oxime acylation and the first reduction may be carried out consecutively or simultaneously. The first reduction is preferably a catalytic hydrogenation and the second reduction is preferably a borohydride reduction.
The invention further relates to novel 2-alkanoylamido-3-oxo-alkanoates and 2-alkanoyloximino-3-oxo-alkanoates which are useful as intermediates for conversion into ceramides.
REFERENCES:
N. P. Singh et al, Journal of Carbohydrate Chemistry, vol. 9, No. 5, 1990, pp. 543-559.
Chemical Abstracts, vol. 54, #5, 1960, 4404i,.
Gregory et al., Journal of Chemical Society, 1951, Letchworth GB, pp. 2453-2456.
Milan Soukup et al, Helvetica Chimica Acta., vol. 70, 1987, Basel Ch pp. 232-236
Hiroshi Kawasaki, Chemical Abstracts, vol. 54, No. 5, 10 Mar. 60, Columbus, Ohio, US, abstract No. 4404i.
Davey Paul N.
Hardinge Brian J.
Newman Christopher P.
Richardson Clive D.
Carr Deborah D.
Dees Jos,e G.
Unilever Patent Holdings B.V.
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