As is clear from Table 1, the method is well suited for the preparation of isomeri-
cally pure 1,3-sn-diacylglycerols with fatty acid residues of widely variable chain
length and also degree of unsaturation.
Due to the simplicity of the purification process by recrystallization, the method is
best suited for the preparation of saturated 1,3-sn-diacylglycerols of moderate (C 8 )to
long (C 18 ) chain lengths.
Isomerically pure 1,3-sn-diglycerides proved to be interesting building blocks for
numerous synthetic applications, most of them related to selective modifications of
the hydroxy group in the 2- position of these molecules. In this respect, we acknowl-
edge the collaboration in this area with the group of Ulbrich-Hofmann (see Chapter
12) (Haftendorn and Ulbrich-Hofmann, 1995; Ulbrich-Hofmann et al., 1998; Haf-
tendorn et al., 2000). Investigations have shown that the 2-hydroxy group of the 1,3-
sn-diglycerides can be:
* replaced by an amino group (Berger, 1993; Haftendorn and Ulbrich-Hofmann,
1995);
* converted into a phosphate group and isomeric phospholipids with an phos-
phoethanolamine function at the 2-position (Haftendorn and Ulbrich-Hofmann,
1995);
6.4 Synthesis of regioisomerically pure 1,3-sn-diglycerides 105
Figure 7. 1,3-Diglycerides from fatty acids.
Figure 8. 1,3-Diglycerides from fatty acid methyl esters.
Figure 9. 1,3-Diglycerides from fatty acid vinyl esters.