Synthesis of chiral diether and tetraether phospholipids: Regiospecific ring opening of epoxy alcohol intermediates derived from asymmetric epoxidation
Journal Article
·
· Journal of Organic Chemistry
- Oregon Graduate Institute of Science & Technology, Beaverton, OR (United States)
Diether and tetraether phospholipids have been synthesized using chiral epoxy alcohol starting materials (e.g. glycidol 3-nitrobenzenesulfonate esters or tert-butyldiphenylsilyl ethers). These chiral precursors provide control over the stereochemistry, substitution patterns, and steric properties of the phosphoglycerol backbone. Configuration at the sn-2 glycerol carbon was controlled by asymmetric epoxidation of allyl alcohol followed by acid-catalyzed, regioselective opening of the oxirane ring using excess aliphatic n-alcohols to give mono-O-alkylated glycerol intermediates in good yields. 9 figs., 5 tabs.
- Sponsoring Organization:
- USDOE
- DOE Contract Number:
- FG06-88ER13963
- OSTI ID:
- 390985
- Journal Information:
- Journal of Organic Chemistry, Vol. 59, Issue 11; Other Information: PBD: 3 Jun 1994
- Country of Publication:
- United States
- Language:
- English
Similar Records
Catalytic asymmetric epoxidation of methyl 7-hydroxy-5E-heptenoate
Epoxidation of lower olefins with hydrogen peroxide and titanium silicalite
Blodgett Forest CA Warming Experiment phospholipid fatty acid and branched glycerol dialkyl glycerol tetraethers data 2018 from: "Whole-soil warming decreases abundance and modifies the community structure of microorganisms in the subsoil but not in surface soil".
Journal Article
·
Wed Apr 20 00:00:00 EDT 1988
· J. Org. Chem. USSR (Engl. Transl.); (United States)
·
OSTI ID:390985
+1 more
Epoxidation of lower olefins with hydrogen peroxide and titanium silicalite
Journal Article
·
Mon Mar 01 00:00:00 EST 1993
· Journal of Catalysis; (United States)
·
OSTI ID:390985
Blodgett Forest CA Warming Experiment phospholipid fatty acid and branched glycerol dialkyl glycerol tetraethers data 2018 from: "Whole-soil warming decreases abundance and modifies the community structure of microorganisms in the subsoil but not in surface soil".
Dataset
·
Fri Jan 01 00:00:00 EST 2021
·
OSTI ID:390985
+5 more