Water → (2S,3R,4R,5S,6R)-2-[3-(Benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran

HRID 550230Notes

Reaction equation

HRID 550230 reaction equation
C([SiH](CC)CC)C.[S:8]1[C:12]([CH2:13][C:14]2[CH:15]=[C:16]([C:24]3(O)[C@H:29]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[C@@H:28]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C@@H:27]([O:46][CH2:47][C:48]4[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=4)[C@@H:26]([CH2:54][O:55][CH2:56][C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[O:25]3)[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][C:10]2[CH:64]=[CH:65][CH:66]=[CH:67][C:9]1=2.O>C(Cl)Cl>[S:8]1[C:12]([CH2:13][C:14]2[CH:15]=[C:16]([C@H:24]3[C@@H:29]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@@H:28]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[C@@H:27]([O:46][CH2:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[C@@H:26]([CH2:54][O:55][CH2:56][C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[O:25]3)[C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:11][C:10]2[CH:64]=[CH:65][CH:66]=[CH:67][C:9]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 12052TriethylsilaneHCID 67156625(3R,4S,5S,6R)-2-[3-(Benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-ol

Product 1

HCID 67157507(2S,3R,4R,5S,6R)-2-[3-(Benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyranYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, triethylsilane (0.34 ml, 2.06 mmol) and a boron trifluoride-diethyl ether complex (0.24 ml, 1.89 mmol) were added dropwise to a solution of (3R,4S,5S,6R)-2-[3-(benzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]-3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydropyran-2-ol (1.4 g, 1.72 mmol) in methylene chloride (15 ml) at 0° C. The reaction mixture was stirred at room temperature for two hours, and then water was added thereto and extracted with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate n-hexane (1:10)] to obtain the title compound (1.1 g, 80.2%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. distillationthe solvent was distilled under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate n-hexane (1:10)]

Sources & evidence

ORD record
ord-7ceb00feb506421c8fc2c7e6c7eaca28
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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