HCID 68873425, compound → HCID 68874491, compound

HRID 1982862Notes

Reaction equation

HRID 1982862 reaction equation
[CH2:1]([O:3][C:4]([O:6][CH2:7][C@H:8]1[O:37][C@@H:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][O:29]CC3C=CC=CC=3)=[CH:23][CH:22]=2)[C@H:11]([OH:38])[C@@H:10]([OH:39])[C@@H:9]1[OH:40])=[O:5])[CH3:2]>C(OCC)(=O)C.C(O)C.[C].[Pd]>[CH2:1]([O:3][C:4]([O:6][CH2:7][C@H:8]1[O:37][C@@H:12]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][OH:29])=[CH:25][CH:26]=2)[C@H:11]([OH:38])[C@@H:10]([OH:39])[C@@H:9]1[OH:40])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 68873425HCID 68873425, compound

Product 1

HCID 68874491HCID 68874491, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[4-(2-benzyloxyethyl)benzyl]phenyl 6-O-ethoxycarbonyl-β-D-glucopyranoside (0.18 g) in ethyl acetate (4 mL) and ethanol (1 mL) was added 10% palladium-carbon powder (0.072 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 18 hours. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1-10/1) to give 2-[4-(2-hydroxyethyl)benzyl]phenyl 6-O-ethoxycarbonyl-β-D-glucopyranoside (0.11 g).

Workup

  1. customInsoluble materials were removed by filtration
  2. customthe solvent of the filtrate was removed under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=20/1-10/1)

Sources & evidence

ORD record
ord-0b16de71e76e4957804dfb0b99e842cb
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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