Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1991-01-22
1994-01-11
Husarik, Nancy S.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 184, 536 185, 536 186, 536122, 536124, 540 2, 540118, C07H 1524, C07H 308, C07J 900
Patent
active
052782964
ABSTRACT:
Novel glycosides, especially steroidal glycosides, and a novel method of their production, are provided. For the novel method of producing novel glycosides, hydroxysteryl compounds are glycosylated with tri-O-acyl glucal using molecular iodine as a reaction catalyst. In this method an alcohol or phenol, especially a hydroxy-steroid such as a water-insoluble cholesterol, is glycosylated, such that the glycosylation is performed in a single step. The resulting steryl pyranoside is by oxidation converted to the corresponding 7-ketosteryl di-O-acyl-pyranoside. The latter pyranoside is selectively reduced to provide the corresponding 7-.beta.-hydroxysteryl 2,3-dideoxy-.alpha.-D-erythro-hex-2-enopyranoside. The steroidal glycosides obtained in this way possess valuable pharmacological properties. In particular, the glycosides in vivo exhibit a selective cell-destructive activity on malignant cells which activity is substantially free of side effects on normal cells. The glycosides also possess a drive-enhancing (stimulating) activity and an anti-inflammatory (immunosuppressive or immunoregulatory) activity.
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Gelman Sciences Inc.
Husarik Nancy S.
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