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US 4,360,694 AGranted
Process for preparing 1,2-diacyl-sn-glycerols
AssigneeKSV-Chemicals Oy
InventorsPaavo K. J. Kinnunen, Tom M. Schroder, Jorma A. Virtanen
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AssigneeKSV-Chemicals Oy
InventorsPaavo K. J. Kinnunen, Tom M. Schroder, Jorma A. Virtanen
Estimating the term…
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.
Process for preparing 1,2-diacyl-sn-glycerols having the formula ##STR11## wherein R.sup.1 and R.sup.2 are the same or different and denote an optionally substituted saturated or unsaturated alkyl group, characterized in that D-mannitol of the formula ##STR12## in a solvent is reacted with a benzene boronic acid of the formula ##STR13## wherein R.sup.3 denotes hydrogen, alkyl, alkoxy or halogen, or with a derivative thereof, and the product obtained, without prior isolation, is reacted with a functional derivative of an acid of the formula ##STR14## wherein R.sup.1 has the meaning given above, in the presence of a tertiary amine, the benzeneboronate protection is removed by hydrolysis or alcoholysis whereby a 1,6-diacyl- or a 1,2,5,6-tetra-acyl-D-mannitol, respectively, is obtained having the formula ##STR15## wherein R.sup.1 has the meaning given above and both R.sup.4 groups are either hydrogen or the acyl group ##STR16## and, in order to prepare a compound of the formula I wherein R.sup.1 .noteq.R.sup.2 the obtained 1,6-diacyl-compound of the formula V is reacted as described above with a benzene boronic acid having the formula III or a derivative thereof and the protected 1,6-diacyl-D-mannitol thus obtained is reacted with a functional derivative of an acid having the formula ##STR17## wherein R.sup.2 has the meaning given above, in the presence of a tertiary amine, the benzeneboronate protection is removed by hydrolysis or alcoholysis, whereby a compound is obtained having the formula ##STR18## wherein R.sup.1 .noteq.R.sup.2, and the 1,2,5,6-tetracyl compound of formula V or of the formula VII is split by oxidation and subsequently reduced with a hydride reducing agent to form the desired compounds of formula I.
In a method of preparing 1,2-diacyl-sn-glycerols, the improvement comprising reacting D-mannitol in a solvent with an optionally substituted benzene boronic acid in the presence of a tertiary amine to produce mannitol-3,4-monobenzene boronate, wherein the benzene boronate can act in subsequent reactions to protect the 3,4 mannitol sites.
The improvement of claim 8, 9, or 10, further comprising the steps of:
Dependencies are inferred from the claim text.