Methanol → HCID 11655639, compound

HRID 550251Notes

Reaction equation

HRID 550251 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]([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]([CH2:54][CH3:55])=[CH:53][C:47]=4[CH:46]=3)[CH:35]=2)[O:14][CH:13]1[CH2:56][O:57]CC1C=CC=CC=1)C1C=CC=CC=1.CO>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]([CH2:54][CH3:55])=[CH:53][C:47]=4[CH:46]=3)[CH:35]=2)[O:14]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 67156415HCID 67156415, compound

Product 1

HCID 11655639HCID 11655639, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, dimethylsulfide (2.66 ml) and a boron trifluoride-diethyl ether complex (1.03 ml, 8.12 mmol) were added to a solution of (3R,4R,5S,6R)-3,4,5-trisbenzyloxy-2-benzyloxymethyl-6-[3-(5-ethylbenzo[b]-thiophen-2-ylmethyl)naphthalen-1-yl]tetrahydropyran (670 mg, 0.81 mmol) in methylene chloride (4 ml) under cooling with ice. The reaction mixture was stirred at room temperature for 1.5 days, and then a 50% methanol aqueous solution (20 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 dried with sodium sulfate, and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methylene chloride:methanol (50:1)] to obtain the title compound (119 mg, 32%).

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 (50:1)]

Sources & evidence

ORD record
ord-3cf8c193a1514fd5ab82deee80947215
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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