Synthesis of enantiomerically pure glyceryl esters and ethers. I. Methods employing the precursor 1,2-isopropylidene-sn-glycerol

✍ Scribed by Hansjörg Eibl; Paul Woolley

• Publisher: Elsevier Science
• Year: 1986
• Tongue: English
• Weight: 491 KB
• Volume: 41
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(86)90124-6

✦ Synopsis

In this and a following paper we describe two complementary strategies for the synthesis of uniform or mixed glyceryl esters and ethers. Using these, virtually any compound of the form l-X-2-Y-3-Z-sn-glycerol can be synthesized, where X, Y and Z are acyl or alkyl groups or may be absent. Yields are high (typically 80%) and the product is enantiomerically pure (racemisation <1%).

The slrategies are based on the use of two different precursors. These papers describe strategies based on the precursor with complementary protection patterns, viz, protection of the sn-1-and -2 positions or of the sn-3 position. In principle all products can be made from either precursor, but the number of steps required may differ considerably: usually, compounds made easily from one precursor are hard to make from the other. This paper describes the strategy based on the precursor 1,2-isopropylidene-sn-glycerol and outlines criteria for the use of different protective groups.

Kcywords. 1,2-isopropylidene-sn-glycerol