The conversion of benzyl 3-O-benzoyl-4,6-O-benzylidene-β-d-galactopyranoside into the 2-benzoate by acyl migration

Add time:09/24/2019    Source:sciencedirect.com

Benzoylation of benzyl 4,6-O-benzylidene-β-d-galactopyranoside (1) with one equivalent of benzoyl chloride in pyridine-dichloromethane solution yields preferentially the 3-benzoate 3. Under alkaline conditions, benzoate 3 can be converted, in high yield, into the 2-benzoate 5, thus providingg an example of acyl migration towards C-1.

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