Further examples of orthoesterification under kinetically controlled conditions. Application to the selective acylation of sucrose, maltose and alpha,alpha-trehalose.
Orthoesterification of sucrose with 1,1-dimethoxyethene under kinetic control gave 4,6-O-methoxyethylidenesucrose in 77% crude yield. Similar orthoesterification of maltose led essentially after acetylation to 1,2,3,6,2',3'-hexa-O-acetyl-4'-6'-O-methoxyethylidenemaltose. Analogous treatment of alpha, alpha-trehalose gave 2,3,2',3'-tetra-O-acetyl-4,6:4',6'-di-O-methoxyethylidene-alpha, alpha-trehalose in 47% yield. The acid-catalyzed opening of these orthoesters was studied, and these reactions were shown to give disaccharides selectively protected by acetyl groups.
Bouchra
M
M
Ecole Nationale Supérieure de Chimie de Clermont-Ferrand, Aubière, France.
Gelas
J
J
D000215:Acylation; D004951:Esterification; D007700:Kinetics; D008320:Maltose / Q000737:chemistry*; D013395:Sucrose / Q000737:chemistry*; D014199:Trehalose / Q000737:chemistry*
D013395:Sucrose; D008320:Maltose; D014199:Trehalose