Certain polyprenyl intermediates

Details Certain polyprenyl intermediates Certain polyprenyl intermediates

1983-02-10

1986-07-29

Rotman, Alan L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546268, 546340, 546344, 546283, 546284, 548146, 560106, 560254, 568 28, 568 32, 568 41, 568 55, 549 14, 549 22, 549 30, 549 39, 549374, 549375, 549416, 549453, 556427, 556428, C07D21371, C07C 69767, C07C 6978, C07C147103

Patent

active

046032088

ABSTRACT:
Novel polyprenyl compounds have the general formula: ##STR1## represents a cis-isoprene unit, n is an integer of 11-19, Z.sup.1 is --CH.sub.2 OH or a functional precursor thereof, and either one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is --S(O).sub.m R.sup.3 in which m is an integer of 0 (zero), 1 or 2 and R.sup.3 is a phenyl, naphthyl, pyridyl or thiazolinyl group or such group substituted with at least one lower alkyl and/or halogen substituent. The topic novel polyprenyl compounds can be synthesized from derivatives of the polyprenol which is obtainable from leaves of Ginkgo biloba or Cedrus deodara, among others, by extraction, if necessary followed by hydrolytic treatment. The novel polyprenyl compounds can be converted to mammalian dolichols or precursors thereof by reductive elimination of the --S(O).sub.m R.sup.3 group.

REFERENCES:
"Dolichol: A Naturally Occurring Isoprenoid Alcohol", Pennock et al., Nature, vol. 186, No. 4723, pp. 470-472, May 1960.
"The High-Performance Liquid-Chromatographic Analysis of Ficaprenol and Dolichol", Keenan et al., Biochem. J. vol. 165, pp. 405-408, (1977).
Biochemical and Biophysical Research Communications, vol. 76, No. 4, pp. 1036-1042, (1977), "Effect of Exogeneous Dolichyl Monophosphate on a Developmental Change in Mannosylphosphoryldolichol Biosynthesis", Harford et al.
"Polyisoprenols in Pinus Sylvestris Needles", Hannus et al., Phytochemistry, vol. 13, pp. 2563-2566, (1974).
"Terpenoids of Pinus Strobus Cortex Tissue", Zinkel et al., Phytochemistry, vol. 11, pp. 3387-3389, (1972).
"Synthese Du Squalene Par Couplage Queue a Queue", Biellmann et al; Tetrahedron Letters, No. 42, pp. 3707-3710, (1969).
"The Tissue and Subcellular Districution of [.sup.3 H]Dolichol in the Rat", Keenan et al; Archives of Biochemistry and Biophysics 179, pp. 634-642, (1977).
"Dolichol: A Naturally-Occurring C.sub.100 Isoprenoid Alcohol", Burgos et al; Biochem. J. 88, pp. 470-483, (1963).
"Desulfonylation of Aryl Alkyl Sulfones", Trost et al; Tetrahedron Letters, No. 39, pp. 3477-3478 (1976).

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