Dimethyl Sulfide → HCID 59869307, compound

HRID 550246Notes

Reaction equation

HRID 550246 reaction equation
CSC.C([O:11][C@@H:12]1[C@H:17]([O:18]CC2C=CC=CC=2)[C@H:16]([O:26]CC2C=CC=CC=2)[CH:15]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[C:36]([CH2:44][C:45]3[S:49][C:48]4[CH:50]=[CH:51][C:52]([O:54][CH3:55])=[CH:53][C:47]=4[CH:46]=3)[CH:35]=2)[O:14][C@@H:13]1[CH2:56][O:57]CC1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:57][CH2:56][C@@H:13]1[C@@H:12]([OH:11])[C@H:17]([OH:18])[C@@H:16]([OH:26])[C@H:15]([C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:37]=[C:36]([CH2:44][C:45]3[S:49][C:48]4[CH:50]=[CH:51][C:52]([O:54][CH3:55])=[CH:53][C:47]=4[CH:46]=3)[CH:35]=2)[O:14]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 516892Sodium BicarbonateHCID 67157186HCID 67157186, compound

Product 1

HCID 59869307HCID 59869307, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, dimethylsulfide (0.66 ml) and a boron trifluoride-diethyl ether complex (0.33 ml, 2.62 mmol) were added to a solution of (2R,3S,4R,5R)-3,4,5-trisbenzyloxy-2-benzyloxymethyl-6-[3-(5-methoxybenzo-[b]thiophen-2-ylmethyl)-naphthalen-1-yl]tetrahydropyran (217 ml, 0.262 mmol) in methylene chloride (4 ml) under cooling with ice. The reaction mixture was stirred at room temperature for three days, and then a saturated sodium hydrogen carbonate aqueous solution was added under cooling with ice and the mixture was extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried with sodium sulfate, and then the solvent was distilled under reduced pressure and the obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (30:1)] to obtain the title compound (85 mg, 65%).

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried with sodium sulfate
  6. distillationthe solvent was distilled under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (30:1)]

Sources & evidence

ORD record
ord-32a77039228c4f04b4ce612faf7b552c
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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