Preparation of alkyl (6R,7S,8R)-6,9-dihydroxy-7,8-isopropylidenedioxy-2,4-nonadienoates and their use for the preparation of D-biotin

US4777273A · kind A · utility

Assignee

• BASF SE

Inventors

• Richard Schmidt · Konstanz, DE
• Martin Maier · Asperg, DE

Key dates

• Filing date: Aug 25, 1986
• Grant date: Oct 11, 1988
• Expiry date: Aug 25, 2006

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D317/30
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Alkyl (6R,7S,8R)-6,9-dihydroxy-7,8-isopropylidenedioxy-2,4-nonadienoates of the formula I ##STR1## where R is alkyl of 1 to 4 carbon atoms are prepared by reacting 3,5-O-isopropylidene-D-arabinose of the formula II ##STR2## with a 3-carboalkoxyprop-2-en-1-ylidene triphenylphosphorane of the formula III ##STR3## in a solvent at elevated temperatures, by a process wherein the reaction is carried out in, as the solvent, a suitable aliphatic or aromatic hydrocarbon, a halogen derivative thereof or a cycloaliphatic ether, preferably an aromatic hydrocarbon of 6 to 8 carbon atoms, at from 65 to 130.degree. C., preferably from 80 to 115.degree. C. Using this process, the basic skeleton of d-biotin can be synthesized from D-arabinose in substantially better yields than obtainable hitherto.