Synthesis of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-mannopyranosyl)-1-propene: a caveat.
During the preparation of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-mannopyranosyl)-1-propene, using a published Sakurai-type reaction on the parent methyl glycoside, some observations were made on the sensitivity to reaction conditions that were not previously reported. This Note presents the study of this allylation reaction followed by acetolysis, which ultimately led to the best conditions to obtain the C-glycoside, and on further transformations to yield the corresponding aldehydic and acidic derivatives.
Girard
Christian
C
Laboratoire de Chimie Bioorganique et de Biotechnologie Moléculaire et Cellulaire, UMR 7001 CNRS, Ecole Nationale Supérieure de Chimie de Paris, F-75005, Paris, France. cgirard@ext.jussieu.fr
Miramon
Marie-Laure
ML
de Solminihac
Tanguy
T
Herscovici
Jean
J
D000107:Acetylation; D000498:Allyl Compounds / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D008362:Mannosides / Q000737:chemistry*; D009005:Monosaccharides / Q000138:chemical synthesis*; D009993:Osmium Tetroxide / Q000737:chemistry; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry; D014297:Trimethylsilyl Compounds / Q000737:chemistry
C472677:3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-mannopyranosyl)-1-propene; D000498:Allyl Compounds; D001593:Benzyl Compounds; D008362:Mannosides; D009005:Monosaccharides; D014297:Trimethylsilyl Compounds; D010504:Periodic Acid; C009288:metaperiodate; D009993:Osmium Tetroxide