Efficient syntheses of 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols from D-pentono-1,4-lactones.
The thioalkylation of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono, and D-xylono-1,4-lactone was performed with the alkylthiol-sodium hydride reagent. The corresponding 5-S-alkyl-5-thio-D-pentono-1,4-lactones were isolated in good yields (82-95%). Reduction with NaBH(4) of these derivatives gave the 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols in 85-96% yields.
Lalot
J
J
Laboratoire des Glucides, Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens, France.
Manier
G
G
Stasik
I
I
Demailly
G
G
Beaupère
D
D
D000478:Alkylation; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000378:metabolism*; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000378:metabolism
D007783:Lactones; D013402:Sugar Alcohols; D013501:Surface-Active Agents