Water → HCID 11547223, compound

HRID 550242Notes

Reaction equation

HRID 550242 reaction equation
CSC.[S:4]1[C:8]([CH2:9][C:10]2[CH:11]=[C:12]([CH:22]3[C@@H:27]([O:28]CC4C=CC=CC=4)[C@@H:26]([O:36]CC4C=CC=CC=4)[C@@H:25]([O:44]CC4C=CC=CC=4)[C@@H:24]([CH2:52][O:53]CC4C=CC=CC=4)[O:23]3)[C:13]3[C:18]([C:19]=2[O:20][CH3:21])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:6]2[CH:61]=[CH:62][CH:63]=[CH:64][C:5]1=2.O>C(Cl)Cl>[S:4]1[C:8]([CH2:9][C:10]2[CH:11]=[C:12]([C@H:22]3[C@H:27]([OH:28])[C@@H:26]([OH:36])[C@H:25]([OH:44])[C@@H:24]([CH2:52][OH:53])[O:23]3)[C:13]3[C:18]([C:19]=2[O:20][CH3:21])=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][C:6]2[CH:61]=[CH:62][CH:63]=[CH:64][C:5]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 1068Dimethyl SulfideHCID 67156759HCID 67156759, compound

Product 1

HCID 11547223HCID 11547223, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, dimethylsulfide (1.6 ml) and a boron trifluoride-diethyl ether complex (0.79 ml, 6.23 mmol) were added to a solution of (3R,4R,5S,6R)-2-[3-(benzo[b]thiophen-2-ylmethyl)-4-methoxynaphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran (515 mg, 0.62 mmol) in methylene chloride (10 ml) under cooling with ice. The reaction mixture was stirred at room temperature for three days, then water (10 ml) 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 (20:1)] to obtain the title compound (82 mg, 28%).

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 (20:1)]

Sources & evidence

ORD record
ord-d73bd2c2158a4d269fc709e5938df97d
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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