Straightforward route for anchoring a glucosyl moiety onto nucleophilic species: reaction of amines and alcohols with carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone.
The base-catalyzed reaction of carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone (prepared from isomaltulose) with amino acids and fatty amines under basic catalysis gave a series of new pseudoglucopeptides, nonionic amphiphiles, and polymerizable derivatives. The same reaction applied to alcohols provided the corresponding 2-(alpha-D-glucopyranosyloxy)acetyl esters with either basic or acidic catalysts.
Trombotto
Stéphane
S
Unité Mixte de Sucrochimie CNRS-Béghin-Say (UMR 143), C/o Béghin-Say, C.E.I., 27 boulevard du 11 novembre 1918, B.P. 2132, 69603 Villeurbanne Cedex, France.
Danel
Mathieu
M
Fitremann
Juliette
J
Bouchu
Alain
A
Queneau
Yves
Y
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002236:Carbohydrate Conformation; D005947:Glucose; D007202:Indicators and Reagents; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D009904:Optical Rotation
D000438:Alcohols; D000475:Alkenes; D000588:Amines; D007202:Indicators and Reagents; D007783:Lactones; C482357:alkolactone A; D005947:Glucose