HCID 68505031, compound → HCID 68506901, compound

HRID 221936Notes

Reaction equation

HRID 221936 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@@:10]21[C:51]1[S:50][C:49]3[C:44](=[CH:45][CH:46]=[CH:47][C:48]=3[CH2:52][C:53]3[CH:58]=[CH:57][C:56]([CH2:59][CH3:60])=[CH:55][CH:54]=3)[C:43]=1[CH2:42][CH2:41][O:40]2)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[CH2:59]([C:56]1[CH:55]=[CH:54][C:53]([CH2:52][C:48]2[CH:47]=[CH:46][CH:45]=[C:44]3[C:49]=2[S:50][C:51]2[C@@:10]4([C@H:9]([OH:8])[C@@H:14]([OH:15])[C@H:13]([OH:23])[C@@H:12]([CH2:31][OH:32])[O:11]4)[O:40][CH2:41][CH2:42][C:43]3=2)=[CH:58][CH:57]=1)[CH3:60]

Participants

5

Reactant 1

HCID 68505031HCID 68505031, compound

Product 1

HCID 68506901HCID 68506901, compoundYield 81.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (1S,3′R,4′S,5′S,6′R)-3′,4′,5′-tris-benzyloxy-6′-benzyloxymethyl-8-[(4-ethylphenyl)methyl]-3,3′,4,4′,5′,6′-hexahydro-spiro[2-oxa-9-thia-fluorene-1,2′-[2H]pyran] (23 mg, 0.028 mmol) in methanol (1 mL) and ethyl acetate (1 mL) was added 10% palladium on carbon (10 mg). The resultant mixture was stirred under a hydrogen atmosphere for 1 hour at room temperature, and the catalyst was then filtered off. Solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (developing solution=dichloromethane:methanol (10:1)), to thereby obtain the titled compound (10.4 mg, 81%).

Workup

  1. filtrationthe catalyst was then filtered off
  2. customSolvent was then removed by distillation under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (developing solution=dichloromethane:methanol (10:1))

Sources & evidence

ORD record
ord-24b16a57b9034b5c9a661d888659e577
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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