Polyprenyl compounds and method of producing the same

Details Polyprenyl compounds and method of producing the same Polyprenyl compounds and method of producing the same

1983-02-17

1986-01-14

Reamer, James H.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2604659, 260404, 2604045, 568410, 568412, 568417, 568448, 564204, 564207, 564509, 564511, 564271, C07C 49203, C09F 500

Patent

active

045644772

ABSTRACT:
There are provided polyprenyl compounds of the formula ##STR1## wherein ##STR2## represent a trans-isoprene unit and a cis-isoprene unit, respectively, n is an integer of 11-19, Z.sup.1 and Z.sup.2 combinedly represent .dbd.O, .dbd.CH--COOH,.dbd.CH--COOR.sup.1, .dbd.CH--CN, .dbd.C(CN)COOR.sup.2, .dbd.CH--CO--NH.sub.2, .dbd.CH--CO--N(R.sup.3) (R.sup.4), .dbd.CH--CO--NHR.sup.5, .dbd.CH--CH.sub.2 --N(R.sup.3) (R.sup.4), .dbd.CH--CH.sub.2 --NHR.sup.5 or .dbd.CH--CHO or Z.sup.1 is a hydrogen atom and Z.sup.2 is --CH.sub.2 COOH, --CH.sub.2 COOR.sup.6, --CH(CN)COOR.sup.2, --CH.sub.2 CN, --CH.sub.2 --CO--NH.sub.2, --CH.dbd.CH--N(R.sup.3) (R.sup.4) or --CH.sub.2 --CH.dbd.N--R.sup.5, R.sup.1, R.sup.2 and R.sup.6 each being a lower alkyl group, R.sup.3 and R.sup.4 each independently being a lower-alkyl, cycloalkyl, aryl or aralkyl group or R.sup.3 and R.sup.4 combinedly representing an alkylene group containing 2-5 carbon atoms, and R.sup.5 being a lower-alkyl, cycloalkyl, aryl or aralkyl group. These polyprenyl compounds can be synthesized starting with a polyprenol obtainable from leaves of a plant such as Ginkgo biloba or Cedrus deodara by extraction and as necessary followed by hydrolysis, or a reactive derivative thereof. The polyprenyl compounds are useful as intermediates for the synthesis of dolichol without the use of an expensive C.sub.5 chain extender.

REFERENCES:
patent: 3326978 (1967-06-01), Dunkel
patent: 4116955 (1978-09-01), Ichikawa et al.
patent: 4386227 (1983-05-01), Sato et al.
Hemming, Chem. Abst., vol. 99, #171383, (1983).
"Dolichol: A Naturally Occurring Isoprenoik Alcohol", Pennock et al.
"The High-Performance Liquid-Chromatographic Analysis of Ficaprenol and Dolichol", Keenan et al.
"Effect of Exogeneous Dolichyl Monophosphate on a Developmental Change in Mannosylphosphoryldolichol Biosynthesis", Harford et al.
"The Tissue and Subcellular Districution of [.sup.3 H]Dolichol in the Rat", Keenan et al.
"Metabolism of Lipid Intermediate in Biosynthesis of Glycoprotein of Regenerated Liver", Hara et al.
"Dolichol: A Naturally-Occurring C.sub.100 Isoprenoid Alcohol", Burgos et al.
"Polyisoprenols in Pinus Sylvestris Needles", Hannus.
"Terpenoids of Pinus Strobus Cortex Tissue", Zinkel et al.
"Synthese Du Squalene Par Couplage Queue a Queue", Biellmann et al.
"Desulfonylation of Aryl Alkyl Sulfones", Trost et al.

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