Sodium Methoxide → HCID 9822503, compound

HRID 1982805Notes

Reaction equation

HRID 1982805 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:34]([O:35]C(=O)C)[C@H:33]([O:39]C(=O)C)[C@@H:32]([CH2:43][O:44]C(=O)C)[O:31][C@H:9]1[O:10][C:11]1[CH:16]=[C:15]([CH2:17][O:18]C(=O)C)[CH:14]=[CH:13][C:12]=1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH3:30])=[CH:25][CH:24]=1)(=O)C>CO>[O:10]([C:11]1[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[CH:13][C:12]=1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:29][CH3:30])=[CH:27][CH:28]=1)[C@@H:9]1[O:31][C@H:32]([CH2:43][OH:44])[C@@H:33]([OH:39])[C@H:34]([OH:35])[C@H:8]1[OH:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 12019997HCID 12019997, compound

Product 1

HCID 9822503HCID 9822503, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (28% methanol solution; 0.3 mL) was added to a solution of 5-acetoxymethyl-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (1.0 g) in methanol (12 mL), and the mixture was stirred at room temperature for 40 minutes. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=7/1) to give 2-(4-ethylbenzyl)-5-hydroxymethylphenyl β-D-glucopyranoside (0.68 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=7/1)

Sources & evidence

ORD record
ord-d6c1c56f4e6349c9856ae1fbf81c2805
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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