(3aR,4R5R,6aS)-4-((S,E)-3-(tert-Butyldimethylsilyloxy)-5-phenylpent-1-enyl)-2-methoxyhexahydro-2H-cyclopenta[b]furan-5-ol → Silanol

HRID 593411

Reaktionsgleichung

Reaktionsgleichung von HRID 593411
[Si:1]([O:8][C@@H:9]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)/[CH:10]=[CH:11]/[C@@H:12]1[C@@H:19]2[C@@H:15]([O:16][CH:17]([O:20]C)[CH2:18]2)[CH2:14][C@H:13]1[OH:22])(C(C)(C)C)(C)C>Cl.C1COCC1>[OH:8][C@@H:9]([CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)/[CH:10]=[CH:11]/[C@@H:12]1[C@@H:19]2[C@@H:15]([O:16][CH:17]([OH:20])[CH2:18]2)[CH2:14][C@H:13]1[OH:22].[SiH3:1][OH:8]

Komponenten

4

Edukt 1

HCID 131734562(3aR,4R5R,6aS)-4-((S,E)-3-(tert-Butyldimethylsilyloxy)-5-phenylpent-1-enyl)-2-methoxyhexahydro-2H-cyclopenta[b]furan-5-ol

Produkt 2

HCID 142154SilanolHCID 587005432H-Cyclopenta[b]furan-2,5-diol, hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl 1-penten-1-yl]-, (3aR,4R,5R,6aS)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18422008HCl tetrahydrofuranLösungsmittel

Versuchsvorschrift

Alcohol 93 (210 mg, 0.485 mmol) was stirred with 1.5% aqueous HCl/THF (3:2) (10 ml) at r.t. for 16 h. The mixture was extracted with CH2Cl2 (5×15 ml) and the combined organic phases were dried (MgSO4), filtered, and concentrated to give the triol 94 and silanol by-product as a clear, colourless oil. This material was taken forward for the subsequent transformation without purification.

Aufarbeitung

  1. extractionThe mixture was extracted with CH2Cl2 (5×15 ml)
  2. dry with materialthe combined organic phases were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-37fa9ac1678947b4b0f5eee9841178f9
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242954B2

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