beta-D-Glucose pentaacetate → 2-(4-methoxycarbonyl-benzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

HRID 1826625Notes

Reaction equation

HRID 1826625 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.C(O[C@@H:23]1[O:40][C@H:39]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[C@@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]1[O:25][C:26](=[O:28])[CH3:27])(=O)C>ClCCl.C1(C)C=CC=CC=1>[C:26]([O:25][C@@H:24]1[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:34]([O:35][C:36](=[O:38])[CH3:37])[C@@H:39]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[O:40][C@H:23]1[O:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)(=[O:28])[CH3:27]

Participants

5

Reactant 2

HCID 2724702beta-D-Glucose pentaacetateHCID 21909287Methyl 4-(2-hydroxybenzyl)benzoate

Product 1

HCID 120855752-(4-methoxycarbonyl-benzyl)phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosideYield 53.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of methyl 4-(2-hydroxybenzyl)benzoate (0.053 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (0.26 g) in dichloromethane (1 mL) and toluene (3 mL) was added boron trifluoride-diethyl ether complex (0.083 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1) to give 2-(4-methoxycarbonylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.067 g).

Workup

  1. additionwas added boron trifluoride-diethyl ether complex (0.083 mL)
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-a1669db2fc8644b6a69ee6d2f3298daf
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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