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-phenylethyl)benzo[b]thiophene

HRID 230886Notes

Reaction equation

HRID 230886 reaction equation
[OH:1][C:2]1[C:10]2[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=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:1][C:2]1[C:10]2[C:9]([CH2:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 10896298alpha-D-Glucopyranose, 2,3,4,6-tetraacetate 1-(2,2,2-trichloroethanimidate)HCID 231035674-Hydroxy-3-(2-phenylethyl)benzo[b]thiophene

Product 1

HCID 671360454-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-(2-phenylethyl)benzo[b]thiopheneYield 40.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-(2-phenylethyl)benzo-[b]thiophene (80 mg), 2,3,4,6-tetra-O-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.17 g) in dichloromethane (3 mL) was added boron trifluoride-diethyl ether complex (0.044 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=2/1-3/2) to give the title compound (75 mg).

Workup

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

Sources & evidence

ORD record
ord-292db5fd6bef49c38834669b19292854
Source dataset
uspto-grants-2009_07
Patent number
US07566699B2

Reaction notes

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