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

HRID 1247749Notes

Reaction equation

HRID 1247749 reaction equation
C([O:4][C@@H:5]1[C@@H:28]([O:29]C(=O)C)[C@H:27]([O:33]C(=O)C)[C@@H:26]([CH2:37][O:38]C(=O)C)[O:25][C@H:6]1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1)(=O)C.C[O-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23][CH3:24])=[O:22])=[CH:17][CH:16]=1)[C@@H:6]1[O:25][C@H:26]([CH2:37][OH:38])[C@@H:27]([OH:33])[C@H:28]([OH:29])[C@H:5]1[OH:4]

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

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) was added sodium methoxide (0.006 g), 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-methoxycarbonyl-benzyl)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-34dca64abd6649b58a69b5b9962d6f3e
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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