Cesium carbonate → HCID 58786179, compound

HRID 1376001Notes

Reaction equation

HRID 1376001 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[C:24]1[CH:33]=[C:32]([CH2:34]Br)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]=1[O:36][CH3:37])(=[O:3])[CH3:2].C1(P(C2CCCCC2)C2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)CCCCC1.[F-].[K+].[C:65](=O)([O-])[O-:66].[Cs+].[Cs+].[O:71]1CCOCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:37][O:36][C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:32]([CH2:34][C:46]2[CH:47]=[C:48]3[C:56](=[CH:55][CH:54]=[CH:53][CH:50]=[CH:49]3)[C:51]=2[C:52]([O:66][CH3:65])=[O:71])=[CH:33][C:24]=1[C@H:6]1[C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7]1

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 522689Potassium FluorideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 58786106HCID 58786106, compound

Product 1

HCID 58786179HCID 58786179, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
85 °C

Procedure

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-(bromomethyl)-1-methoxy-2-naphthyl]-D-glucitol (0.62 g) was added to a suspension of methyl 2-(tributylstanyl)azulene-1-carboxylate (0.25 g), tris(dibenzylideneacetone)dipalladium (0) (0.05 g), 2-(dicyclohexylphosphino)biphenyl (0.05 g), potassium fluoride (0.09 g), and cesium carbonate (0.35 g) in 1,4-dioxane (20.0 ml). The mixture was stirred at 60° C. for eight hours and at 85° C. for further 14 hours. Insoluble matters were removed by filtration, the filtrate was evaporated to remove the solvent. The residue was purified by silica gel column chromatography to obtain methyl 2-[(4-methoxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy) methyl]tetrahydro-2H-pyran-2-yl]-1-naphthyl)methyl]azulene-1-carboxylate (0.34 g).

Workup

  1. customInsoluble matters were removed by filtration
  2. customthe filtrate was evaporated
  3. customto remove the solvent
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c6086e79881a4c4e9775d9da9e8127b0
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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