Dimethyl Sulfide → HCID 11626638, compound

HRID 550238Notes

Reaction equation

HRID 550238 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)[C@@H:15]([CH2:34][O:35]CC2C=CC=CC=2)[O:14][CH:13]1[C:43]1[C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=[C:45]([CH2:53][C:54]2[S:58][C:57]3[CH:59]=[CH:60][C:61]([F:63])=[CH:62][C:56]=3[CH:55]=2)[CH:44]=1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:63][C:61]1[CH:60]=[CH:59][C:57]2[S:58][C:54]([CH2:53][C:45]3[CH:44]=[C:43]([C@H:13]4[C@H:12]([OH:11])[C@@H:17]([OH:18])[C@H:16]([OH:26])[C@@H:15]([CH2:34][OH:35])[O:14]4)[C:52]4[C:47]([CH:46]=3)=[CH:48][CH:49]=[CH:50][CH:51]=4)=[CH:55][C:56]=2[CH:62]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 516892Sodium BicarbonateHCID 67156466HCID 67156466, compound

Product 1

HCID 11626638HCID 11626638, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, dimethylsulfide (1.72 ml) and a boron trifluoride-diethyl ether complex (0.86 ml, 6.8 mmol) were added to a solution of (3R,4R,5S,6R)-3,4,5-trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-fluorobenzo[b]-thiophen-2-ylmethyl)naphthalen-1-yl]tetrahydropyran (550 mg, 0.68 mmol) in methylene chloride (15 ml) under cooling with ice. The reaction mixture was stirred at room temperature for 2.5 days, 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 then dried with sodium sulfate, and thereafter the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (40:1)] to obtain the title compound (140 mg, 46%).

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 (40:1)]

Sources & evidence

ORD record
ord-66369d874b4741948880cc3e35b0a4f9
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

Loading…