beta-D-Glucose pentaacetate → HCID 12085619, compound

HRID 1826660Notes

Reaction equation

HRID 1826660 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH2:11])=[O:10])=[CH:7][CH:6]=1.C(O[C@@H:22]1[O:39][C@H:38]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[C@@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:23]1[O:24][C:25](=[O:27])[CH3:26])(=O)C>C1(C)C=CC=CC=1>[C:25]([O:24][C@@H:23]1[C@@H:28]([O:29][C:30](=[O:32])[CH3:31])[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@@H:38]([CH2:40][O:41][C:42](=[O:44])[CH3:43])[O:39][C@H:22]1[O:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[CH2:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](=[O:10])[NH2:11])=[CH:7][CH:6]=1)(=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 2724702beta-D-Glucose pentaacetateHCID 21909273HCID 21909273, compound

Product 1

HCID 12085619HCID 12085619, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-(2-hydroxybenzyl)benzamide (0.063 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (0.33 g) in toluene (3 mL) was added boron trifluoride diethyl-ether complex (0.11 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-carbamoylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside. To a solution of the obtained 2-(4-carbamoylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in methanol (5 mL) was added sodium methoxide (0.005 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/ethanol=5/1) to give 2-(4-carbamoylbenzyl)phenyl β-D-glucopyranoside (0.068 g).

Workup

  1. additionwas added boron trifluoride diethyl-ether complex (0.11 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-dcb971fed8bb4b48b7aa8955a21f44a1
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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