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A surprising C-4 epimerization of 5-deoxy-5-sulfonylated pentofuranosides under Ramberg-Bäcklund reaction conditions
Tarun Kumar Pal1, Tanmaya Pathak
1Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Abstract:
Treatment of methyl 5-deoxy-2,3-O-isopropylidene-5-(benzylsulfonyl)-β-D-ribofuranoside with CBr(2)F(2)-KOH/Al(2)O(3) afforded the corresponding olefinic sugar. The methyl- and the isopropyl-analogues in contrast underwent epimerization at C-4 to generate the α-L-lyxo derivatives.
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