Ammonium Chloride → (3R,4R,5S,6R)-3,4,5-Trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-ethylbenzo[b]thiophen-2-yl-methyl)naphthalen-1-yl]tetrahydropyran-2-ol

HRID 550250Notes

Reaction equation

HRID 550250 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH2:23][C:24]2[S:28][C:27]3[CH:29]=[CH:30][C:31]([CH2:33][CH3:34])=[CH:32][C:26]=3[CH:25]=2)[CH:14]=1.[CH2:35]([O:42][CH:43]1[CH:48]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH:47]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[CH:46]([CH2:65][O:66][CH2:67][C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[O:45][C:44]1=[O:74])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[Cl-].[NH4+]>C1COCC1>[CH2:35]([O:42][C@@H:43]1[C@H:48]([O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C@@H:47]([O:57][CH2:58][C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)[C@@H:46]([CH2:65][O:66][CH2:67][C:68]2[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=2)[O:45][C:44]1([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH2:23][C:24]2[S:28][C:27]3[CH:29]=[CH:30][C:31]([CH2:33][CH3:34])=[CH:32][C:26]=3[CH:25]=2)[CH:14]=1)[OH:74])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 45855083,4,5-Tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-oneHCID 671572602-(4-Bromonaphthalen-2-ylmethyl)-5-ethylbenzo[b]thiopheneHCID 178418244HCID 178418244, compound

Product 1

HCID 67157378(3R,4R,5S,6R)-3,4,5-Trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-ethylbenzo[b]thiophen-2-yl-methyl)naphthalen-1-yl]tetrahydropyran-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 0.83 ml, 1.33 mmol) was added dropwise to a solution of 2-(4-bromonaphtalen-2-ylmethyl)-5-ethylbenzo-[b]thiophene (460 mg, 1.21 mmol) in THF (15 ml) at −78° C. The reaction mixture was stirred at the same temperature for five minutes and to this solution, a solution of 3,4,5-trisbenzyloxy-6-benzyloxymethyltetrahydro-pyran-2-one (844 mg, 1.57 mmol) in THF (5 ml) was added dropwise. The reaction solution was stirred at −78° C. for five minutes and a saturated ammonium chloride aqueous solution was added to stop the reaction. The reaction mixture was extracted with ethyl acetate and 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 (1:9)] to obtain the title compound (1.06 mg, 100%).

Workup

  1. stirringThe reaction solution was stirred at −78° C. for five minutes
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. distillationthe solvent was distilled under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:9)]

Sources & evidence

ORD record
ord-20bcf1c9c81e4041a2cdefb7a5782c73
Source dataset
uspto-grants-2011_05
Patent number
US07943748B2

Reaction notes

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