HCID 66765671, compound → HCID 66765806, compound

HRID 556782Notes

Reaction equation

HRID 556782 reaction equation
[CH3:1][C:2]1[CH:56]=[CH:55][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C@@H:16]4[O:45][C@H:44]([CH2:46][O:47]CC5C=CC=CC=5)[C@@H:35]([O:36]CC5C=CC=CC=5)[C@H:26]([O:27]CC5C=CC=CC=5)[C@H:17]4[O:18]CC4C=CC=CC=4)[CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1>O1CCCC1.CO.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C@@H:16]4[O:45][C@H:44]([CH2:46][OH:47])[C@@H:35]([OH:36])[C@H:26]([OH:27])[C@H:17]4[OH:18])[CH:14]=3)[CH:9]=[CH:8]2)=[CH:55][CH:56]=1

Participants

5

Reactant 1

HCID 66765671HCID 66765671, compound

Product 1

HCID 66765806HCID 66765806, compound

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[1-(4-methylbenzyl)-1H-indol-6-yl]-1-deoxy-2,3,4,6-tetra-O-benzyl-β-D-glucopyranose and 10% palladium-carbon powder (0.12 g) in tetrahydrofuran (3 mL) and methanol (3 mL) was stirred at room temperature for 1 hour under a hydrogen atmosphere. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.035 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-bad55bf9d0d040e5866c407b23ed030a
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

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