Process for the manufacture of 3-amino-substituted glycosylated

Details Process for the manufacture of 3-amino-substituted glycosylated Process for the manufacture of 3-amino-substituted glycosylated

1997-03-24

1999-01-26

Weber, Jon P.

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

Organic compounds

Carbohydrates or derivatives

536 185, 536124, C07J 300, C07G 300, C07G 1700

Patent

active

058640223

ABSTRACT:
The present invention relates to a process for the preparation and manufacture of 3-amino-substituted glycosylated bile acid derivatives. Intermediates and related compounds are also disclosed. In particular, the present invention permits the conversion of cholic acid esters to the 3-amino-7,12-bis(glucosyl)cholic acid esters via an azide intermediate. Conditions for the purification and isolation of the desired product is also disclosed to provide an overall manufacturing process suitable for large-scale production.

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Per-Mikael .ANG.berg, et al. -Large Scale Synthesis of Two Trisaccharide Spacer Glycosides Corresponding to the Blood Group A and B Determinants Using Thioglysosides and Dimethyl (Thiomethyl) Sulfonium Tetrafluoroborate (DMTSB) as Promoter--J. Carb. Chem. 13(2), p. 141-161, (1994).
Wolf et al. "Intramolecular Catalysis. VI. Selectivity in 7alpha, 12alpha-Dihydroxy Steroids and Enhancement of 12 alpha-Hydroxyl Reactivity by Substituents at Carbon 3, " J. Org. Chem. (1973) 38(3): 1276-1279.

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