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

HRID 1078133Notes

Reaction equation

HRID 1078133 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:17]([OH:36])[C@H:18]([OH:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Rh]>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:17]([OH:36])[C@H:18]([OH:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 452451L-Iditol, 1,2,5,6-tetradeoxy-2,5-bis(((1,1-dimethylethoxy)carbonyl)amino)-1,6-diphenyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 15093367(2S,3R,4R,5S)-2,5-Di-(N-((t-butyloxy)carbonyl)amino)-1,6-dicyclohexyl-3,4-dihydroxyhexaneYield 65%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 180 mg (0.36 mmol) 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.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3113e3835cd544b3b388618cd7075c2d
Source dataset
uspto-grants-1996_08
Patent number
US05545750

Reaction notes

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