Abstract
The reaction of derivatives of 3-acetyl- d-glucal, 3-acetyl- l-rhamnal, 3-acetyl- d-galactal, and 3-acetyl- d-lactal with sodium benzenesulfinate in acid medium catalyzed by HgSO 4 afforded diastereoisomeric mixtures of the corresponding 2,3-dideoxy-3-(phenylsulfonyl)-hexopyranoses through a Ferrier rearrangement. The anomeric alkoxyl radical fragmentation of these γ-hydroxy sulfones using the system (diacetoxyiodo)benzene and iodine gave vinyl sulfones with structures of 1,2-dideoxy-4- O-formyl-2-(phenylsulfonyl)-pent-1-enitol and configurations d- erythro, l- erythro, and d- threo at the two stereogenic centers.
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