1,2,3,5-Tetraacetyl-beta-D-ribofuranose → 2-Amino-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole

Participants

Reaction Conditions

Reaction Steps

2-Amino-5,6-dichlorobenzimidazole (4) (3 g, 16 mmole) was dissolved in dry acetonitrile (150 ml) and stirred in an inert atmosphere at 60° C. BSA (4.37 ml, 17 mmole) was added and the mixture was stirred for 10 minutes. 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5.09 g, 16 mmole) and TMSTf (3.29 ml, 17 mmole) were added to the clear solution and the mixture was allowed to stir at 60° C. for 1 hr. The mixture was concentrated under reduced pressure and separated on a silica column to yield 1.14 g (15%) of 2-amino-5,6-dichloro-1-(2,3,5,tri-O-acetyl-βribofuranosyl)benzimidazole (43).

Provenance & Evidence