作者
Carmen R Alonso-Cruz, Elisa I Leon, Francisco J Ortiz-Lopez, María S Rodríguez, Ernesto Suárez
发表日期
2005/8/8
期刊
Tetrahedron letters
卷号
46
期号
32
页码范围
5265-5268
出版商
Pergamon
简介
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 HgSO4 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.
引用总数
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