Process for preparing 1,2-diacyl-sn-glycerols

Details Process for preparing 1,2-diacyl-sn-glycerols Process for preparing 1,2-diacyl-sn-glycerols

1981-04-06

1982-11-23

Killos, Paul J.

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

Organic compounds

Carboxylic acid esters

560264, 2604106, 2604107, 549453, 549454, C09F 508, C11C 302, C07C 6702

Patent

active

043606946

ABSTRACT:
The object of the present invention is a novel and simple process for the production of 1,2-diacyl-sn-glycerols, wherein the acyl groups may be the same or different. According to the invention D-mannitol is reacted with benzene boronic acid or a derivative thereof to form a D-mannitol-monobenzeneboronate which compound is acylated either to form, after removal of the benzeneboronate protective group, a 1,2,5,6-tetraacyl-D-mannitol with four identical acyl groups, or is acylated selectively in two stages, by first acylating the 1,6-hydroxy groups of the boronate protected D-mannitol to form, after removal of the boronate protection, a 1,6-diacyl-D-mannitol, which then is repeatedly reacted with a benzene boronic acid or a derivative thereof and then acylated in the 2- and 5-positions. After removal of the boronate protective group, the tetra-acylated D-mannitol obtained either in the one-stage or two-stage process is split by oxidation to form a 1,2-diacyl-glyceraldehyde which in turn is reduced to the corresponding 1,2-diacyl-sn-glycerol. By means of the invention it is thus possible to prepare 1,2-diacyl-sn-glycerols in which the acyl groups can be the same or different.

REFERENCES:
patent: 2290609 (1942-07-01), Goss
patent: 3772357 (1973-11-01), Hamanaka

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