A surprising C-4 epimerization of 5-deoxy-5-sulfonylated pentofuranosides under Ramberg-Bäcklund reaction conditions.
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.
Pal
Tarun Kumar
TK
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India.
Pathak
Tanmaya
T
D000537:Aluminum Oxide / Q000737:chemistry*; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D006878:Hydroxides / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D017680:Potassium Compounds / Q000737:chemistry*; D012263:Ribonucleosides / Q000737:chemistry*
D002241:Carbohydrates; D005663:Furans; D006878:Hydroxides; D017680:Potassium Compounds; D012263:Ribonucleosides; D000537:Aluminum Oxide; C029943:potassium hydroxide