Solid-phase de novo synthesis of a (+/-)-2-deoxy-glycoside.
The solid-phase synthesis of methyl 2-deoxy-3-O-benzyl-D,L-arabino-hexopyranoside was achieved in a six-step sequence via a de novo strategy based on the hetero-Diels-Alder reaction of a vinyl ether supported on an azalactone-functionalized polystyrene resin, followed by the functional modification of the heteroadduct and the final release of the methyl glycoside by acidic solvolysis.
Lucchesi
Céline
C
UCO2M, UMR 6011 Centre National de la Recherche Scientifique, Université du Maine, Faculté des Sciences, Avenue Olivier Messiaen, Le Mans Cedex 9, France.
Arboré
Amélie
A
Pascual
Sagrario
S
Fontaine
Laurent
L
Maignan
Christian
C
Dujardin
Gilles
G
D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D006027:Glycosides