Debenzylation and detritylation by bromodimethylborane: synthesis of mono-acid or mixed-acid 1,2- or 2,3-diacyl-sn-glycerols.
A novel method of deprotecting primary alcohols protected with either benzyl or trityl groups by using bromodimethylborane under mild reaction conditions (dichloromethane, -20 to 5 degrees C) has been applied to the synthesis of optically pure mono-acid or mixed-acid 1,2- or 2,3-diacyl-sn-glycerols. This method was particularly useful for the synthesis of long saturated acyl (C12 to C24) as well as unsaturated diacyl-sn-glycerols since little or no acyl migration occurred during deprotection. Diacylation of 3-benzyl-sn-glycerol or 1-benzyl-sn-glycerol followed by bromodimethylborane debenzylation gave mono-acid 1,2- or 2,3-diacyl-sn-glycerols, respectively. The mixed-acid 1,2- or 2,3-diacyl-sn-glycerols were prepared from 1-acyl-sn-glycerols or 3-acyl-sn-glycerols, respectively, by tritylation, acylation with a different fatty acid, followed by detritylation with bromodimethylborane.
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Biophysics Department, Housman Medical Research Center, Boston University School of Medicine, MA 02118-2394.
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D001555:Benzene Derivatives / Q000737:chemistry; D001880:Boranes; D004075:Diglycerides / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D014320:Triphenylmethyl Compounds / Q000737:chemistry
D001555:Benzene Derivatives; D001880:Boranes; D004075:Diglycerides; D007202:Indicators and Reagents; D014320:Triphenylmethyl Compounds