L-Iditol, 1,2,5,6-tetradeoxy-2,5-bis(((1,1-dimethylethoxy)carbonyl)amino)-1,6-diphenyl- → (2S,3R,4R,5S)-2,5-Di-(N-((t-butyloxy)carbonyl)amino)-1,6-dicyclohexyl-3,4-dihydroxyhexane

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Reaction Steps

A mixture of 180 mg (0.36mmol) of (2S,3R, 4R, 5S)-2,5-di-(N-((t-butyloxy)carbonyl)amino)-3,4-dihydroxy-1,6-diphenylhexane and 180 mg of 5% rhodium on carbon in 50 ml of methanol was shaken under 4 atmospheres of hydrogen for 24 h. The resulting mixture was filtered and concentrated in vacuo. The residue was purified by silica gel chromatography using 5% ethyl acetate in hexane to provide 120 mg (65%) of the desired compound (Rf 0.35, 30% ethyl acetate in hexane) as a white solid, m.p. 224°-226° C. Mass spectrum: (M+H)+ =513.

Provenance & Evidence