alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate) → 4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-methylphenyl)ethyl]benzofuran

HRID 230873Notes

Reaction equation

HRID 230873 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:20]([O:23][C@@H:24]1[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:35]([O:41][C:42](=[O:44])[CH3:43])[C@@H:34]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:33][C@@H:25]1OC(=N)C(Cl)(Cl)Cl)(=[O:22])[CH3:21]>ClCCl>[C:20]([O:23][C@@H:24]1[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:35]([O:41][C:42](=[O:44])[CH3:43])[C@@H:34]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:33][C@H:25]1[O:1][C:2]1[C:7]2[C:8]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 23103572HCID 23103572, compound

Product 1

HCID 671363594-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-[2-(4-methylphenyl)ethyl]benzofuranYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-[2-(4-methylphenyl)ethyl]-benzofuran (0.13 g) and 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.27 g) in dichloromethane (5 mL) was added boron trifluoride-diethyl ether complex (0.069 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1-3/2) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-methylphenyl)ethyl]benzofuran (0.25 g). This material was dissolved in methanol (4 mL). To the solution was added sodium methoxide (28% methanol solution, 0.082 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give the title compound (0.14 g).

Workup

  1. customThe reaction mixture was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1-3/2)

Sources & evidence

ORD record
ord-b13ea95333e542bdb56b4434b3a314ac
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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