Glycerol monoacyl derivs

Glycerol Monoacyl Derivatives were prepd before WWII by IGFarbenindustrie AG, FrP 848740 (1931) CA, 35, 5912(1941), on heating Glycidol Nitrate, QI2.0.CH.CHa(QNO2) with. an org acid... 

In addition to kinetic resolution processes, the previously described peptide-catalysed acylation reaction of alcohols can be applied to desymmetrisation of meso compounds. In 2005, Miller and coworkers published the desymmetrisation of prochiral glycerol derivatives via enantioselective acylation of one primaiy alcohol function. A (3-tum histidine-based pentapeptide was identified as the most promising catalyst from a peptide libraiy and afforded the monoacylated product with up to 97% enantiomeric excess. One year later Miller and Hansen successfully demonstrated the desymmetrisation of a meso bis-phenol compound, which was found to be challenging because of the large distance between the two OH groups as well as between the desired site of functionalisation and the prochiral stereogenic centre of the substrate. The nucleophilic N-methylhistidine containing peptide 9 was identified as a powerful tool for monoacylation via extensive libraiy... 

The mass spectra of TMS ether derivatives of monoacyl-, monoalkyl- and monoalk-l-enyl-glycerols have been described [43]. Diradylglycerols may also be tri-methylsilylated, and the mass spectra have structurally informative features [44-47]. 

A novel glycolipid (12) isolated from the extreme thermoacidophile Bacillus acidocaldarius is a 2-acylamino-2-deoxy-j3-D-glucopyranosyl derivative of 1,2,3,4-tetrahydroxypentane linked to hopane (a pentacyclic triterpene) at C-29. Three other glycolipids possess a common structure (13) having the hydroxy-groups of their glycerol residues unsubstituted, or monoacylated, or diacylated. 

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