beta-D-Glucose pentaacetate → HCID 12085573, compound

HRID 1982813Notes

Reaction equation

HRID 1982813 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1.C(O[C@@H:26]1[O:43][C@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:27]1[O:28][C:29](=[O:31])[CH3:30])(=O)C>ClCCl.C1(C)C=CC=CC=1>[C:29]([O:28][C@@H:27]1[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@@H:42]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:43][C@H:26]1[O:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8](/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:10]=1)(=[O:31])[CH3:30]

Participants

5

Reactant 2

HCID 2724702beta-D-Glucose pentaacetateHCID 12085536HCID 12085536, compound

Product 1

HCID 12085573HCID 12085573, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of ethyl (E)-3-[4-(2-hydroxybenzyl)-phenyl]acrylate (0.34 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (1.4 g) in dichloromethane (3 mL) and toluene (9 mL) was added boron trifluoride diethyl ether complex (0.45 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 (E)-2-[4-(2-ethoxycarbonylvinyl)benzyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.47 g). To the solution of the obtained (E)-2-[4-(2-ethoxycarbonylvinyl)-benzyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.46 g) in methanol (5 mL) was added sodium methoxide (0.010 g), and the resulting 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 (E)-2-[4-(2-ethoxycarbonylvinyl)benzyl]phenyl β-D-glucopyranoside (0.31 g).

Workup

  1. additionwas added boron trifluoride diethyl ether complex (0.45 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-01b96ee83a8e41bb92ca70123e92b88b
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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