Résumé
Treatment of methyl 5-acetamido-2,4,7,8,9-penta-
O-acetyl-3,5-dideoxy-β-
d-
glycero-
d-
galacto-2-nonulopyranosonate (
1) severally with thiophenol, phenylmethanethiol, and ethanethiol in the presence of boron trifluoride etherate gave the corresponding 2-thio-β-glycosides
3–5. Treatment of methyl (5-acetamido-4,7,8,9-tetra-
O-acetyl-3,5-dideoxy-β-
d-
glycero-
d-
galacto-2-nonulopyranosyl chloride)onate (
2) severally with thiophenol in the presence of
N,N-di-isopropylethylamine,
O-ethyl
S-potassium dithiocarbonate, and
O-ethyl
S-potassium thiocarbonate gave the corresponding 2-thio-α-glycosides
7, 10, and
11, of which
10 was converted into the ethyl 2-thio-α-glycoside
9 on heating with
N,N-dimethylformamide-sodium iodide. The phenyl 2-thioglycosides
3 and
7 were converted into the corresponding sulfones.