Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof
Patent
1999-08-16
2000-11-14
Gerstl, Robert
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfonic acids or salts thereof
564343, C07C27100, C07C30914
Patent
active
061472530
ABSTRACT:
N-protected/N-substituted alpha-amino aldehydes, which are useful as pharmaceuticals and pharmaceutical intermediates, can be stored and shipped in a more stable form as N-protected/N-substituted-beta-amino hydroxy sulfonates which can be readily converted back into the aldehyde under mild conditions. The present invention relates to N-protected/N-substituted-beta-amino hydroxy sulfonates and their preparation and use.
REFERENCES:
patent: 4990669 (1991-02-01), Reetz et al.
Parikh, et al., "Sulfur Trioxide in the Oxidation of Alcohols by Dimethyl Sulfoxide," J. Am. Chem. Soc., 89:21, 5505-5507, Oct. 11, 1967.
Mancuso, et al., "Oxidation of Long-Chain and Related Alcohols to Carbonyls by Dimethyl Sulfoxide `Activiated` by Oxalyl Chloride," J. Org. Chem., vol. 43, No. 12, 2480-2482, 1978.
Rittle, et al., "A Synthesis of Statine Utilizing an Oxidation Route to Chiral .alpha.-Amino Aldehydes," J. Org. Chem., vol. 47, 3016-3018, 1982.
Dellaria, et al., "The Enation- and Diastereoselective Synthesis of the First Phospho-Statine Derivative," Tetrahedron Letters, vol. 27, No. 21., 2337-2340, 1986.
Garner,et al., "The Synthesis and Configurational Stability of Differentially Protected .beta.-Hydroxy-.alpha.-amino Aldehydes," J. Org. Chem., vol. 52, 2361-2364, 1987.
Reetz, et al., "Tandem Aldolization/Lactonization/Dyotropic Rearrangement of .alpha.-Amino-Aldehydes," Tetrahedron Letters, vol. 30, No. 40., 5421-5424, 1989.
Jurczak, et al., "Optically Active N-Proctected .alpha.-Amino Aldehydes in Organic Synthesis," Chem. Rev., vol. 89, 149-164, 1989.
Reetz, et al., "Stereoselective Reactions of Chiral .alpha.-Amino Aldehydes," Phil. Trans. R. Soc. Lond., A 326, 573-578 (1988).
Hamada, et al., "New Methods and Reagents in Organic Synthesis, A Practical Method for the Preparation of Optically Active N-Protected .alpha.-Amino Aldehydes and Peptice Aldehydes " Chem. Pharm. Bull, 30(5) 1921-1924, 1982.
Lubell, et al., "Configurational Stability of N-Protected .alpha.-Amino Aldehydes," J. Am. Chem. Soc., 109, 236-239, 1987.
Reetz, et al., "Stereoselective Synthesis of .beta.-Amino Alcohols from Optically Active .alpha.-Amino Acids," Angew. Chem. Int. Ed. Engl. 26, No. 11, 1987.
Khusid, "Regeneration of Aldehydes from Their Bisulfite Derivatives in Water and Organic Solvents On Ion-Exchange Resins," J. Org. Chem. of the USSR, vol. 21, No. 1, 37-39.
Erman, et al., "Structure and Properties of the Bisulfite Adducts of Citral," J. Org. Chem. of the USSR, vol. 15, No. 8, 1246-1431.
Ingles, "Preparation of Bisulphite Addition Compounds of 5-amino-5-deoxy-D-xylose," Australian J. of Org. Chem., vol. 19, No. 4, 667-673.
International Search Report dated Apr. 14, 1997.
G. D. Searle & Co.
Gerstl Robert
LandOfFree
N-protected/N-substituted-beta-amino-hydroxy sulfonates does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with N-protected/N-substituted-beta-amino-hydroxy sulfonates, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-protected/N-substituted-beta-amino-hydroxy sulfonates will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2066860