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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
ノート
印刷プレビュー

反応式

HRID 1037729 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 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

生成物 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-carboxylate収率 97%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b5325f3f7e874da7b4fa3d5d9c27aa40
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546603B2

反応ノート

読み込み中…

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