Solid-phase synthesis of sn-1,2- and sn-2,3-diacylglycerols via ring-opening of the glycidyl-bound resin.
A general method developed for the parallel solid-phase synthesis of sn-1,2- and sn-2,3-diacyglycerol derivatives. The technique relies on the use of carboxylic acid-promoted epoxide ring-opening reactions of the glycidyl-bound resin 3. The polymer-bound monoacylglycerol 5, formed in this manner, is transformed to the respective polymer-bound diacylglycerols 7 and 9 by reaction of the free alcohol moiety with a second carboxylic acid under conditions that lead to retention or inversion of C-2 stereochemistry. The sequence is completed by BCl3-promoted cleavage of 7 and 9 to form the sn-1,2- and sn-2,3-diacylglycerols, respectively.
Seo
Jin-soo
JS
Medicinal Science Division, Korea Research Institute of Chemical Technology, PO Box 107, Yusung-gu, Daejeon, 305-600, Korea.
Yoon
Cheol Min
CM
Gong
Young-Dae
YD
D002264:Carboxylic Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry; D004853:Epoxy Resins / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D002264:Carboxylic Acids; D004075:Diglycerides; D004853:Epoxy Resins