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 1982844Notes

Reaction equation

HRID 1982844 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-trichloroacetoimidoyl-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, and to the residue was added ethanol. The resulting precipitates were collected by filtration and 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
  3. additionto the residue was added ethanol
  4. customThe resulting precipitates
  5. filtrationwere collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-9f0dc89c92fe44c3a8355c7211531a01
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

Loading…