Preparation of alkyl (6R,7S,8R)-6,9-dihydroxy-7,8-isopropylidene

Details Preparation of alkyl (6R,7S,8R)-6,9-dihydroxy-7,8-isopropylidene Preparation of alkyl (6R,7S,8R)-6,9-dihydroxy-7,8-isopropylidene

1986-08-25

1988-10-11

Chan, Nicky

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D31730

Patent

active

047772735

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.

REFERENCES:
patent: 4450276 (1984-05-01), Gelhaus et al.
Vogel et al. (Liebigs Ann. Chem. 1980, 1972-77).
M. Maier (cf. Degree Thesis, University of Konstanz, 1981).
Chemical Abstract 98:107081c (1983) equivalent to DE 3122562.
Chemical Abstract 98:34422c (1983).
Chemical Abstracts Band 94, Nr. 15, Apr. 13, 1981, Columbus, Ohio, USA: F. Vogel et al. "(+)-Biotin from D-arabinose", Seite 688, Spalte 2, Abstract Nr. 121 407 n & Liebigs Ann. Chem. Band 1980, Nr. 12, Seiten 1972-1977 (Kat. D).
Martin Maier, "Entwicklung Einer Kurzen und Effektiven Biotinsynthese".

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