Synthesis of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-α-d-mannopyranosyl)-1-propene: a caveat

During the preparation of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-α-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.