Efficient syntheses of 1-bromodeoxy-, 1-azidodeoxy- and 1-aminodeoxypentitols from unprotected D-pentono-1,4-lactones.
The reduction of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono and D-xylono-1,4-lactones was achieved with NaBH4 in water-EtOH. The corresponding 1-bromo-1-deoxypentitols were isolated after acetylation in good overall yields (60-90%). 1-Azido-1-deoxypentitols were obtained quantitatively either by nucleophilic substitution by azide ion and deacetylation of the corresponding monobromopentitols or by reduction of the corresponding 5-azido-5-deoxy-D-pentono-1,4-lactones. The reduction of the monoazidopentitols by catalytic hydrogen transfer gave the monoaminopentitol analogues in quantitative yield.
Bouchez
V
V
Laboratoire de Chimie Organique, Université de Picardie Jules Verne, Amiens, France.
Stasik
I
I
Beaupère
D
D
D000606:Amino Sugars / Q000138:chemical synthesis*; D001386:Azides / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D013402:Sugar Alcohols / Q000138:chemical synthesis*
D000606:Amino Sugars; D001386:Azides; D007783:Lactones; D013402:Sugar Alcohols