Sodium Methoxide → 2-(4-methoxycarbonylbenzyl)phenyl beta-D-glucopyranoside

HRID 1982824Notes

Reaction equation

HRID 1982824 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:31]([O:32]C(=O)C)[C@H:30]([O:36]C(=O)C)[C@@H:29]([CH2:40][O:41]C(=O)C)[O:28][C@H:9]1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=1)(=O)C>CO>[O:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([O:26][CH3:27])=[O:25])=[CH:20][CH:19]=1)[C@@H:9]1[O:28][C@H:29]([CH2:40][OH:41])[C@@H:30]([OH:36])[C@H:31]([OH:32])[C@H:8]1[OH:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 120855752-(4-methoxycarbonyl-benzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Product 1

HCID 674597572-(4-methoxycarbonylbenzyl)phenyl beta-D-glucopyranosideYield 85.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.006 g) was added to a solution of 2-(4-methoxycarbonylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.066 g) in methanol (5 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate) to give 2-(4-methoxycarbonylbenzyl)phenyl β-D-glucopyranoside (0.040 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-9fa7f734fcdf42d19f96b2afd835973c
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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