Abstract
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°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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 169-173 |
| Number of pages | 5 |
| Journal | Chemistry and Physics of Lipids |
| Volume | 61 |
| Issue number | 2 |
| DOIs | |
| State | Published - Apr 1992 |
Bibliographical note
Funding Information:This work was supported by National Institutes of Health research grant HL-26335 and training grant HL-07291 and with financial support from the Whitaker Health Sciences Fund.
Keywords
- acyl migration
- bromodimethylborane
- debenzylation
- detritylation
- diacyl-sn-glycerol synthesis