alpha-D-Glucopyranosyl bromide, tetraacetate → HCID 69423446, compound

HRID 916572Notes

Reaction equation

HRID 916572 reaction equation
[C:1]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:21][C:22]([O:24][CH2:25][C@H:26]1[O:31][C@H:30](Br)[C@H:29]([O:33][C:34]([CH3:36])=[O:35])[C@@H:28]([O:37][C:38]([CH3:40])=[O:39])[C@@H:27]1[O:41][C:42]([CH3:44])=[O:43])=[O:23]>ClCCl.C(=O)([O-])[O-].[Ag+2]>[C:1]([NH:4][C:5]1[N:10]=[C:9]([O:11][C@@H:30]2[O:31][C@H:26]([CH2:25][O:24][C:22](=[O:23])[CH3:21])[C@@H:27]([O:41][C:42](=[O:43])[CH3:44])[C@H:28]([O:37][C:38](=[O:39])[CH3:40])[C@H:29]2[O:33][C:34](=[O:35])[CH3:36])[C:8]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 22934954HCID 22934954, compound

Product 1

HCID 69423446HCID 69423446, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(N-acetylamino)-3-(4-ethylbenzyl)-1H-pyridin-2-one (0.034 g) in dichloromethane (2.5 mL) were added acetobromo-α-D-glucose (0.10 g) and silver carbonate (0.17 g), and the mixture was stirred under shading for 3 hours at 50° C. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=1/2) to give 6-(N-acetylamino)-2-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-3-(4-ethylbenzyl)pyridine (0.081 g).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative thin layer chromatography on silica gel (developing solvent: hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-91edf2d4bb5449b688f11c25513123da
Source dataset
uspto-grants-2007_09
Patent number
US07271153B2

Reaction notes

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