THE ACTION OF THIOLS ON DERIVATIVES OF D-XYLOSE

Article abstract of DOI:10.1016/S0008-6215(00)85539-1

The action of thiols on 1,2,3,4-tetra-O-acetyl β-D-xylopyranose gave 2- and 5-alkylthiopentose dithioacetals and alkyl 1-thio-D-xylopyranosides.On treatment with thiols and trifluoroacetic acid, 3-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose derivatives rapidly formed 4-O-acetyl-2,3-dialkylthio-D-ribose dithioacetal derivatives, which were in turn converted into 4-O-acetyl-3-S-benzyl-2,5-epithio-3-thio-D-ribose (or D-arabinose) dithioacetal.