Azobisisobutyronitrile → 3,6-anhydro-1,2-dideoxy-1-(diethoxyphosphinyl)-1,1-difluoro-4,5,7-tris-O-(phenylmethyl)-D-manno-heptitol

Participants

Reaction Steps

A 440 mg portion of a mixture of 3,6-anhydro-1-deoxy-1-(diethoxyphosphinyl)-1,1-difluoro-4,5,7-tris-O-(phenylmethyl)-D-glycero-D-galacto-heptitol, O-1H-imidazole-1-carbothioate and 2,5-anhydro-7-deoxy-7-(diethoxyphosphinyl)-7,7-difluoro-1,3,4-tris-O-(phenylmethyl)-D-glycero-D-manno-heptitol, O-1H-imidazole-1-carbothioate was dissolved in 12 ml of dry toluene, then treated with 900 μl of n-tributyl stannous hydride and a few crystals of 2,2'-azobisisobutyronitrile and heated in an oil bath under argon for 3 hours. The solution was cooled, then stored in a freezer and finally evaporated. The resulting oil was purified by chromatography giving the desired compound.

Provenance & Evidence