Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Patent
1988-10-31
1990-04-10
Sutto, Anton H.
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
558 87, 558 88, 585351, 560128, 562510, C07F 940
Patent
active
049162500
ABSTRACT:
Novel phosphonate compounds of the formula ##STR1## are disclosed and claimed, as well as methods for manufacturing the phosphonates from C-14 through C-16 aldehydes. The phosphonate compounds of the present invention can be employed to form 13-cis retinoic acid, retin-A and beta-carotene.
REFERENCES:
patent: 3600473 (1971-08-01), Sarmatis
patent: 4175204 (1979-11-01), Babler
Bourguignon, J. J. and C. G. Wermuth, "Lactone Chemistry. Synthesis of Beta-Substituted, Gamma-Functionalized Butanolides and Butenolides and Succinaldehydic Acids from Glyoxylic Acid", J. Org. Chem. (1981), 46, pp. 4889-4894.
Czekanski, T., H. Gross and B. Contisella, "Methandiphosphonsaureester durch UV-Induzierte Michaelis-Becker-Reaktion", 35, J. f. prakt. Chemie. Band 324, Heft 4 (1982), pp. 537-544.
Curley, R. W., Jr. and C. J. Ticoras, "Stereospecific Synthesis of the Important Retinoid Synthon Ethyl trans-3-Formyl-2-butenoate via Direct Two-Stage Oxidation of Ethyl 3-Methyl-2-butenoate", J. Org. Chem. (1986), 51, pp. 256-258.
Isler, O., W. Huber, A. Ronco and M. Kofler, "Synthese des Vitamin A", Helv. Chim. Acta, 30, 1947, vol. XXX, pp. 1911-1927.
Julia, M. and D. Arnould, "Synthese a l'aide de Sulfones, III Syntheses de la vitamine A", Bull. Soc. Chim. Fr. (1973), Part 2, pp. 746-750.
Laugraud, S., A. Guingant and J. d'Angelo, "A Direct Route for the Synthesis of (E)-3-Alkyl-4-Oxo-2-butenoic Acid Esters", J. Org. Chem. (1987), 52, pp. 4788-4790.
Liu, R. S. H. and A. E. Asato, Tetrahedron Report No. 165, "Photochemistry and Synthesis of Stereoisomers of Vitamin A", Tetrahedron, vol. 40, No. 11 (1984), pp. 1931-1969.
Pattenden, G. and B. C. L. Weedon, "Carotenoids and Related Compounds. Part XVIII, Synthesis of Cis and D-Cis-Polyenes by Reactions of the Wittig Type", J. Chem. Soc. (C) (1968), pp. 1984-1997.
Pommer, H. and R. Kuhn, "Synthesen in der Carotinoid-Reihe", Angew. Chem., 72 (1960), No. 23, pp. 911-915.
Rammamurthy, V., G. Tustin, C. C. Yau and R. S. H. Liu, "Preparation of Sterically Hindered Geometric Isomers of 7-Cis-Beta-Ionyl and Beta-Ionylidene Derivatives in the Vitamin A Series", Tetrahedron, vol. 31 (1975), pp. 193-199.
Reif, W. and H. Grassner, "Die Technische Vitamin-A-Synthese der BASF", Chemie-Ing.-Techn., 45 (1973)m No. 10a, pp. 646-652.
Rosenberger, M., W. Jackson and G. Saucy, "The Synthesis of Beta, Gama and Alpha, Beta-Unsaturated Aldehydes via Polyene Epoxides", Helvetica Chimica Acta, vol. 63, Fasc. 6 (1980), No. 175, pp. 1665-1674.
Surmatis, J. D. and R. Thommen, "The Synthesis of Trans-Beta-Carotene from Retinyl Phosphonate by the Michaelis-Arbuzov Reaction", J. Org. Chem., vol. 34, No. 3 (1969), pp. 559-560.
Loyola University of Chicago
Sutto Anton H.
LandOfFree
Phosphonate reagent compositions does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Phosphonate reagent compositions, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phosphonate reagent compositions will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2300129