3376-49-6Relevant articles and documents
Biomimetic monoacylation of diols in water. Lanthanide-promoted reactions of methyl benzoyl phosphate
Cameron, Lisa L.,Wang, Sheila C.,Kluger, Ronald
, p. 10721 - 10726 (2004)
The direct monoacylation of diols by acyl phosphate monoesters in water is a biomimetic analogy to the enzymic aminoacylation of tRNA by aminoacyl adenylates. Without catalysis, acyl phosphate monoesters react rapidly with amines but very slowly with water and alcohols. Lanthanide ions dramatically and selectively facilitate the base-catalyzed monoacylation of diols in water by methyl benzoyl phosphate (MBP), a typical acyl phosphate monoester, in neutral solutions where reactive amines are protonated and unreactive. The reaction patterns and reactivity of various diols with MBP in the presence of lanthanides are consistent with a mechanism that involves internal addition from the conjugate base of the bis-bidentate complex of the lanthanide with the diol and MBP. The method is also applicable to reactions of nucleosides as evidenced by the selective monoacylation of the 2′- or 3′-hydroxyl group of adenosine, without reaction of the 5′-hydroxyl group or the 6-amino group. Analogues of adenosine without the diol are unreactive. This suggests that the method will selectively monoacylate the hydroxyl groups at the unique diol in tRNA that forms the 3′-terminus.
Desymmetrization of meso-glycerol derivatives induced by L -histidine-derived acylation catalysts
Sakakura, Akira,Umemura, Shuhei,Ishihara, Kazuaki
supporting information; experimental part, p. 1938 - 1942 (2011/10/08)
The desymmetrization of meso-glycerol derivatives bearing a 3-pyrroline-1-carbonyl (Pyroc) directing group is demonstrated through an enantioselective acylation reaction promoted by L-histidine-derived bifunctional catalysts. The desired monoacylated products are obtained in good yields (up to 74%) with high enantioselectivities (up to 99% ee). Copyright
Regioselective opening of an oxirane system with trifluoroacetic anhydride. A general method for the synthesis of 2-monoacyl- and 1,3-symmetrical triacylglycerols
Stamatov, Stephan D.,Stawinski, Jacek
, p. 3659 - 3669 (2007/10/03)
A trifluoroacetic anhydride-catalyzed opening of the oxirane system of glycidyl esters with a simultaneous migration of the acyl group provides a new, efficient entry to either 2-monoacylglycerols (2-MAG) or 1,3-symmetrical triglycerides (1,3-STG) as potential prodrug frameworks.
