Triethylsilane → HCID 67156466, compound

HRID 550237Notes

Reaction equation

HRID 550237 reaction equation
C([SiH](CC)CC)C.[CH2:8]([O:15][C@@H:16]1[C@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:18][C:17]1([C:48]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[C:50]([CH2:58][C:59]2[S:63][C:62]3[CH:64]=[CH:65][C:66]([F:68])=[CH:67][C:61]=3[CH:60]=2)[CH:49]=1)O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:8]([O:15][C@H:16]1[C@@H:21]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:20]([O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C@@H:19]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[O:18][CH:17]1[C:48]1[C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH:51]=[C:50]([CH2:58][C:59]2[S:63][C:62]3[CH:64]=[CH:65][C:66]([F:68])=[CH:67][C:61]=3[CH:60]=2)[CH:49]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 67157082HCID 67157082, compound

Product 1

HCID 67156466HCID 67156466, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, triethylsilane (0.19 ml, 1.21 mmol) and a boron trifluoride-diethyl ether complex (0.14 ml, 1.11 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-2-ol (770 mg, 0.93 mmol) in methylene chloride (10 ml) at 0° C. The reaction mixture was stirred at room temperature for two hours, and then a saturated sodium hydrogen carbonate aqueous solution was added. The obtained mixture was extracted with methylene chloride, and the organic layer was washed with a saturated sodium chloride aqueous solution and then dried with sodium sulfate. The solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:20)] to obtain the title compound (550 mg, 73%).

Workup

  1. extractionThe obtained mixture was extracted with methylene chloride
  2. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried with sodium 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 (1:20)]

Sources & evidence

ORD record
ord-95b520b3c4064edb8738a3308a029228
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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