N-protected/N-substituted-beta-amino hydroxy sulfonates

Details N-protected/N-substituted-beta-amino hydroxy sulfonates N-protected/N-substituted-beta-amino hydroxy sulfonates

1998-07-09

1999-08-17

Gerstl, Robert

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

Organic compounds

Amino nitrogen containing

C07C27100

Patent

active

059395877

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 `Activated` 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 Enatino- And Diastereoselective Synthesis of the First Phospho-Statine Derivative," Tetrahedron Letters, vol. 27, No. 21., 2337-2340, 1986.
Garner,et al., "The Synthesis and Configruational 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-Protected .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.
March, Advanced Organic Chemistry, 895, 1992.
International Search Report dated Apr. 14, 1997.

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