Efficient synthesis of 5-thio-D-arabinopyranose and 5-thio-D-xylopyranose from the corresponding D-pentono-1,4-lactones.
5-Thio-D-arabinopyranose (5) and 5-thio-D-xylopyranose (10) were synthesized from the corresponding D-pentono-1,4-lactones. After regioselective bromination at C-5, transformation into 5-S-acetyl-5-thio derivatives, reduction into lactols and deprotection afforded the title compounds in 49 and 42% overall yield, respectively.
Lalot
Jérôme
J
Laboratoire des Glucides, Université de Picardie Jules Verne, 33 Rue Saint-Leu, F-80039 Amiens, France.
Stasik
Imane
I
Demailly
Gilles
G
Beaupère
Daniel
D
D001089:Arabinose / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D014994:Xylose / Q000031:analogs & derivatives / Q000138:chemical synthesis*
C488016:5-thioarabinopyranose; C488017:5-thioxylopyranose; D007783:Lactones; D014994:Xylose; D001089:Arabinose