Patent · US Expired

Preparation of retinyl glycosides and intermediates therefor

US5126500A · kind A · utility

2Cited by

2References

8Claims

0Family size

Assignee

BASF SE

Inventors

Ulrich von Deessen · Speyer, DE
Joachim Paust · Schifferstadt, DE
Klaus Kaiser · Neustadt, DE
Helmut Indest · Weinheim, DE

Key dates

Filing date	Jan 28, 1991
Grant date	Jun 30, 1992
Priority date	—
Expiry date	Jan 28, 2011

Classification

Technology area (CPC Y)Emerging Cross-Sectional Technologies
CPC primaryY02P20/55
WIPO fieldOrganic fine chemistry
WIPO sectorChemistry

Abstract

A process for preparing retinyl glycosides of the formula I ##STR1## where Z is a glycosidic residue, by glycosidation of a completely acylated carbohydrate or completely acylated glycosidic polymer of the formula II EQU Z (acylated)-Y (II) where Y is a leaving group customary for glycosidations in the 1-position of the glycoside, comprises the acylated glycoside being reacted with an aldehyde-protected 4-hydroxy-2-methyl-2-buten-1-al under the conditions customary for glycosidations, eliminating the aldehyde protective group from the resulting compound, subjecting the resulting aldehyde to a Wittig reaction with a .beta.-ionylideneethyltriphenylphosphonium salt and eliminating the acyl groups on the resulting retinyl glycoside in a conventional manner. The process according to the invention is particularly important for preparing retinyl glycosides of the formula Ia ##STR2## where R is --CH.sub.2 --OH, --COOH or --COOCH.sub.3. Intermediates of this process are also claimed.

Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.