Ethanethiol → HCID 131723781, compound

Participants

Reaction Steps

1,2,4,6-Tetra-O-acetyl-3-O-methyl-α-L-idopyranose (prepared as described for its per-benzoyl analogue by replacing benzoyl chloride with acetic anhydride; Jaurand et al. Bio. Med. Chem. Lett, 1992, 2, 897-900) (48.4 g) is dissolved in toluene (175 ml). Ethanethiol (20 ml) and boron trifluoride etherate (1M in toluene, 134 ml) are added under a nitrogen atmosphere. After stirring for 1 hour, aqueous sodium hydrogen carbonate (400 ml) and the mixture is added and the mixture is stirred for 1 hour. The mixture is then poured into ethyl acetate. The organic phase is washed twice with water and concentrated. Purification by chromatography on a column of silica gel gives 29.6 g of compound 52.

Provenance & Evidence