alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) → 2-(4-methoxybenzyl)-3,5-dimethyl-phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

HRID 1247740Notes

Reaction equation

HRID 1247740 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[OH:16])=[CH:5][CH:4]=1.[C:19]([O:22][C@@H:23]1[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:32][C@@H:24]1OC(=N)C(Cl)(Cl)Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([O:22][C@@H:23]1[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:32][C@H:24]1[O:16][C:9]1[CH:10]=[C:11]([CH3:15])[CH:12]=[C:13]([CH3:14])[C:8]=1[CH2:7][C:6]1[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 120856032-(4-Methoxybenzyl)-3,5-dimethylphenol

Product 1

HCID 120856042-(4-methoxybenzyl)-3,5-dimethyl-phenyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosideYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-methoxybenzyl)-3,5-dimethylphenol (4.0 g) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroaceto-imidoyl-α-D-glucopyranose (8.9 g) in dichloromethane (100 mL) was added boron trifluoride diethyl-ether complex (2.5 mL) at 0° C., and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: dichloromethane). The solvent was removed under reduced pressure, ethanol was added to the residue, and the resulting crystals were collected by filtration. The obtained crystals were dried under reduced pressure to give 2-(4-methoxybenzyl)-3,5-dimethylphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (7.8 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on aminopropyl silica gel (eluent: dichloromethane)
  2. customThe solvent was removed under reduced pressure, ethanol
  3. additionwas added to the residue
  4. filtrationthe resulting crystals were collected by filtration
  5. customThe obtained crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-c739dcea9fca44b68d0022aeef1e724c
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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