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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → Methyl 5-(3-((1R,2R,3R,5R)-5-chloro-2-((3S,7R,E)-3,7-dihydroxyoct-1-enyl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylate

HRID 1037729
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HRID 1037729 반응식
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Si]([O:25][C@@H:26]([CH3:59])[CH2:27][CH2:28][CH2:29][C@H:30]([OH:58])/[CH:31]=[CH:32]/[C@H:33]1[C@H:37]([O:38]C2CCCCO2)[CH2:36][C@@H:35]([Cl:45])[C@@H:34]1[CH2:46][CH2:47][CH2:48][C:49]1[S:53][C:52]([C:54]([O:56][CH3:57])=[O:55])=[CH:51][CH:50]=1)(C(C)(C)C)(C)C>CO>[Cl:45][C@H:35]1[C@H:34]([CH2:46][CH2:47][CH2:48][C:49]2[S:53][C:52]([C:54]([O:56][CH3:57])=[O:55])=[CH:51][CH:50]=2)[C@@H:33](/[CH:32]=[CH:31]/[C@@H:30]([OH:58])[CH2:29][CH2:28][CH2:27][C@H:26]([OH:25])[CH3:59])[C@H:37]([OH:38])[CH2:36]1
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참가 물질

4

반응물 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57734122Methyl 5-(3-((1R,2R,3R,5R)-2-((3S,7S,E)-7-(tert-butyldimethylsilyloxy)-3-hydroxyoct-1-enyl)-5-chloro-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)propyl)thiophene-2-carboxylate

생성물 1

HCID 57734135Methyl 5-(3-((1R,2R,3R,5R)-5-chloro-2-((3S,7R,E)-3,7-dihydroxyoct-1-enyl)-3-hydroxycyclopentyl)propyl)thiophene-2-carboxylate수율 97%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

Pyridinium p-toluenesulfonate (20.4 mg, 0.081 mmol) was added to a solution of the THP-ether 15 (52 mg, 0.081 mmol) in MeOH (3 mL) at 23° C. The reaction was stirred for 24 h and then concentrated in vacuo. The residue was diluted with EtOAc and washed with 1N HCl, saturated aqueous NaHCO3 and brine. The organic portion was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by FCC (silica gel, 19:1 EtOAc/MeOH) to afford 34.9 mg (97%) of triol 11.

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with 1N HCl, saturated aqueous NaHCO3 and brine
  4. dry with materialThe organic portion was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by FCC (silica gel, 19:1 EtOAc/MeOH)

출처 및 근거

ORD 기록
ord-b5325f3f7e874da7b4fa3d5d9c27aa40
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546603B2

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