Sodium Hydroxide → 2-(4-carboxybenzyl)phenyl beta-D-glucopyranoside

HRID 1247752Notes

Reaction equation

HRID 1247752 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]C)=[O:22])=[CH:17][CH:16]=1)(=O)C.[OH-].[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]([OH:23])=[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 14798Sodium HydroxideHCID 120855752-(4-methoxycarbonyl-benzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Product 1

HCID 674584912-(4-carboxybenzyl)phenyl beta-D-glucopyranosideYield 111.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(methoxycarbonyl)benzyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.050 g) in methanol (1 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.26 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography on benzenesulfonylpropyl silica gel (eluent: methanol) to give 2-(4-carboxybenzyl)phenyl β-D-glucopyranoside (0.038 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on benzenesulfonylpropyl silica gel (eluent: methanol)

Sources & evidence

ORD record
ord-b6299f99c64e45da9f07277cbc311e4d
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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