A surprising C-4 epimerization of 5-deoxy-5-sulfonylated pentofuranosides under Ramberg–Bäcklund reaction conditions

Pal, Tarun Kumar ; Pathak, Tanmaya (2008) A surprising C-4 epimerization of 5-deoxy-5-sulfonylated pentofuranosides under Ramberg–Bäcklund reaction conditions Carbohydrate Research, 343 (16). pp. 2826-2829. ISSN 0008-6215

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/j.carres.2008.08.010

Abstract

Treatment of methyl 5-deoxy-2,3-O-isopropylidene-5-(benzylsulfonyl)-β-D-ribofuranoside with CBr2F2–KOH/Al2O3 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.

Item Type:Article
Source:Copyright of this article belongs to Elsevier Science.
Keywords:Sulfonylated Carbohydrates; Ramberg–Bäcklund Reaction; SO2-extrusion; Olefinic Sugar; Epimerization
ID Code:104101
Deposited On:17 Mar 2017 10:26
Last Modified:17 Mar 2017 10:26

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