Thio linked glycosyl compounds

Details Thio linked glycosyl compounds Thio linked glycosyl compounds

1993-03-19

1996-05-07

Nutter, Nathan M.

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

Organic compounds

Carbohydrates or derivatives

536 181, C07G 300, C07G 1100, C07H 1500, C07H 1700

Patent

active

055147844

ABSTRACT:
Thio linked glycosyl compounds are disclosed and synthesized. The synthesis employs a blocked carbohydrate donor and a blocked glycosyl acceptor. The carbohydrate donor includes an acid labile phosphite leaving group attached to the anomeric carbon. The blocked glycosyl acceptor includes an unprotected thio group susceptible to electrophilic attack. The reaction is initiated by the addition of a Lewis acid so as to activate the acid labile phosphite leaving group on the carbohydrate donor. The substitution reaction may be conducted at -78.degree. C. in a solvent such as Et.sub.3 N which favors the formation of thio linked glycosylation products.

REFERENCES:
patent: 4189471 (1980-02-01), Pon Pipom et al.
patent: 4229441 (1980-10-01), Bugianesi et al.
patent: 4301152 (1981-11-01), Ponpipom
patent: 4310505 (1982-01-01), Baldeschwieler et al.

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