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

HRID 550236노트

반응식

HRID 550236 반응식
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]([F:33])=[CH:32][C:26]=3[CH:25]=2)[CH:14]=1.[CH2:34]([O:41][CH:42]1[CH:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH:46]([O:56][CH2:57][C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[CH:45]([CH2:64][O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[O:44][C:43]1=[O:73])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Cl-].[NH4+]>C1COCC1>[CH2:34]([O:41][C@@H:42]1[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@@H:46]([O:56][CH2:57][C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C@@H:45]([CH2:64][O:65][CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[O:44][C:43]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]([F:33])=[CH:32][C:26]=3[CH:25]=2)[CH:14]=1)[OH:73])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 45855083,4,5-Tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-oneHCID 671565772-(4-Bromonaphthalen-2-ylmethyl)-5-fluorobenzo[b]thiopheneHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 67157437(3R,4S,5S,6R)-3,4,5-Trisbenzyloxy-6-benzyloxymethyl-2-[3-(5-fluorobenzo[b]thiophen-2-ylmethyl)naphthalen-1-yl]tetrahydropyran-2-ol수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In a nitrogen stream, an n-butyllithium hexane solution (1.6 M, 0.97 ml, 1.55 mmol) was added dropwise to a solution of 2-(4-bromonaphthalen-2-yl-methyl)-5-fluorobenzo[b]thiophene (520 mg, 1.41 mmol) in THF (15 ml) at −78° C. and the reaction mixture was stirred at the same temperature for 10 minutes. To this solution, a solution of 3,4,5-trisbenzyloxy-6-benzyloxymethyl-tetrahydropyran-2-one (835 mg, 1.55 mmol) in THF (3 ml) was added dropwise. The mixture was stirred at −78° C. for one hour, and a saturated ammonium chloride aqueous solution was added thereto to stop the reaction. The reaction mixture was extracted with ether, 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 (1:20)] to obtain the title compound (770 mg, 66%).

후처리

  1. stirringThe mixture was stirred at −78° C. for one hour
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ether
  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 (1:20)]

출처 및 근거

ORD 기록
ord-e1fcc83317c5462b99a40d19af15ac35
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943748B2

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