Solvolytic behaviors of O-benzoyl, cyclic O,O-thionocarbonate, and O,S- thiolcarbonate groups in 3-O-benzoyl-1,2-O-isopropylidene-α-d-glucofuranose derivatives

Article abstract of DOI:10.1248/cpb.44.1476

O-Benzoyl, cyclic thionocarbonate, and thiolcarbonate groups in 5,6-O- thiono-, 5,6-O,S-thiol-, and 5,6-S,O-thiolcarbonates of 3-O-benzoyl-1,2-O- isopropylidene-α-D-glucofuranoses behaved differently on solvolysis under alkaline conditions. Generally, the 3-O-benzoyl group was the most vulnerable to NaOH in water or MeOH, while thionocarbonate and thiolcarbonate groups were more reactive than the O-benzoyl group toward methanolysis with NaOMe. In particular, methanolysis of the 5,6-S,O- thiolcarbonate with NaOMe gave a thiirane derivative very rapidly.

Full text of DOI:10.1248/cpb.44.1476

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