Process for the preparation of 2-aminoalkane-1,3,4-triols

Details Process for the preparation of 2-aminoalkane-1,3,4-triols Process for the preparation of 2-aminoalkane-1,3,4-triols

1996-10-15

1999-11-30

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564355, 564503, C07C21500

Patent

active

059945869

ABSTRACT:
The subject of the invention is a process for the preparation of 2-aminoalkane-1,3,4-triols, in a single stage, preferably a single reduction state, from alkyl 2-hydroxyimino-3-oxo-4-acyloxyalkanoates. The invention makes possible a significant reduction in the number of stages and a marked improvement in the synthesis yields.

REFERENCES:
M. Viscontini, "Reduction des substances Beta-amino-alpha, gamma-dicarbonylees; une nouvelle synthese de l'allo-DL-phenyl-3-amino-2-propane-diol-1,3 (DL-erythro-phenylserinol)," Helvetica Chimica Acta, vol. XXXV, Oct. 1952, pp. 1803-1805.
March, "Reduction of Nitroso Compounds and Hydroxylamines to Amines," Advanced Organic Chemistry, 1985, John Wiley & Sons, 3d Ed., p. 1105.
Houben-Weyl, "Reduktion von Oximen (Isonitros overbindungen) und Hyroxylaminen," Methoden der Organischen Chemie, vol. XI/1, 1957, pp. 495-506.
Sisido et al., "Synthesis of Racemic Phytophingosine and the lyxoIsomer," Journal of Organic Chemistry, vol. 34, No. 11, Nov. 1969, pp 3539-3544.
Chemical Abstracts, vol. 98, No. 1, Jan. 3, 1983, "Reactions of Esters of Alpha-(Bromoacyl)Acetic Acid with Sodium Thioacetate," p. 4452, Column R, Abstract No.4551u.
Journal of the Chemical Society, Perking Transactions 1, No. 2, Feb. 1987, pp. 333-343, Leslie Crombie et al.., "Synthesis of the Mammea Coumarins, Part 2, Experiments in the Mammea E Series and Synthesis of Mammea E/AC".
Journal of Organic Chemistry, vol. 43, No. 10, May 12, 1978, pp. 2087-2088, Yuji Oikawa et al., "Meldrum's Acid in Organic Chemistry 2: A General and Versatile Synthesis of Beta-Keto Esters".
C. A. 95:132261 (1981).

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