Thiosugars. VII. Synthesis of Methyl 2, 3, 5, 6-Tetradeoxy-2, 3, 5, 6-tetrathio-β-L-galactofuranoside and -a-D-Altrofuranoside

Abstract

The 5, 6-dimethanesulfonyl derivative (2) of methyl 2, 3-di-S-benzyl-2, 3-dideoxy-2, 3-dithio-α-D-altrofuranoside (1) reacted with sodium ethyl xanthate to give methyl 2, 3-di-S-benzyl-2, 3, 5, 6-tetradeoxy-2, 3-dithio-5, 6-(thiocarbonyl) dithio-β-L-galactofuranoside (3) and -α-D-altrofuranoside (4). Reduction of 3 and 4 with liquid ammonia-metallic sodium gave methyl 2, 3, 5, 6-tetradeoxy-2, 3, 5, 6-tetrathio-β-L-galactofuranoside (5) and -α-D-altrofuranoside (6), respectively.