Abstract
Methyl α- d-mannopyranoside (1 mole) reacts with 2,2-dimethoxypropane (1 mole), to give the 4,6- O-isopropylidene derivative ( 2) which rearranges to the 2,3- O-isopropylidene derivative ( 4). Compound 4 can also be prepared by graded hydrolysis of methyl 2,3:4,6-di- O-isopropylidene-α- d-mannopyranoside. Successive benzoylation, oxidation, and reduction of 4 provides a useful route to a number of d-talopyranoside compounds. Methyl α- d-mannofuranoside (1 mole) reacts with 1–2 moles of 2,2-dimethoxypropane to give the 5,6- O-isopropylidene derivative ( 16) in 90% yield.
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