Tin tetrachloride → HCID 86673682, compound

Participants

Reaction Steps

To a mixture consisting of Compound 27A (10 molar equivalents) in an appropriate solvent is added SnCl4 (equimolar) in dichloroethane. A mixture consisting of (2S,3R,4R,5R)-5-((2S,5S)-2-azido-6-(tert-butoxy)-5-(4-methylphenylsulfonamido)-6-oxohexyl)tetrahydrofuran-2,3,4-triyl triacetate (limiting reagent, prepared in the manner of Rapoport et. al. as 25β) is added and the mixture stirred at room temperature for 16 hours. The mixture is partitioned between ethyl acetate and 0.5N Na2HPO4 and the organics washed with brine, dried and evaporated. The residue is chromatographed on silica gel to obtain the title intermediate.

Provenance & Evidence