Isobutyric anhydride → methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate

HRID 3027

Reaktionsgleichung

Reaktionsgleichung von HRID 3027
I/[CH:2]=[CH:3]/[C@@H:4]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:5][C@H:6]([CH3:11])[CH2:7][CH2:8][CH2:9][CH3:10].[C:20]([Li])([CH3:23])([CH3:22])[CH3:21].C([Cu])#CCCCC.C([C@H:36]1[CH2:40][C:39](=[O:41])[C:38]([S:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][C:48]([O:50][CH3:51])=[O:49])=[C:37]1O[SiH](C)C)(C)(C)C.[C:56]([O:61]C(=O)C(C)C)(=O)[CH:57]([CH3:59])[CH3:58]>CN(C)P(N(C)C)N(C)C>[CH3:51][O:50][C:48](=[O:49])[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][S:42][C:38]1[C@@H:37](/[CH:2]=[CH:3]/[C@@H:4]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:5][C@H:6]([CH3:11])[CH2:7][CH2:8][CH2:9][CH3:10])[C@H:36]([O:12][Si:13]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:15])[CH3:14])[CH2:40][C:39]=1[O:41][C:56](=[O:61])[CH:57]([CH3:59])[CH3:58]

Komponenten

7

Edukt 5

HCID 7346Isobutyric anhydrideHCID 15689554(1E,3S,5R)-1-iodo-3-(tert-butyldimethylsiloxy)-5-methyl-1-noneneHCID 131720587(4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonylpentylthio)-2-cyclopenten-1-oneHCID 178418306HCID 178418306, VerbindungHCID 178418419C6H9Cu

Produkt 1

HCID 22883798methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15355Hexamethylphosphorous triamideLösungsmittel

Versuchsvorschrift

Using as the materials and reagents (1E,3S,5R)-1-iodo-3-(tert-butyldimethylsiloxy)-5-methyl-1-nonene (476 mg, 1.2 mmol), tert-butyllithium (1.54 mol/l, 1.56 ml, 2.4 mmol), 174 mg of 1-hexynylcopper, hexamethylphosphorous triamide (436 μl), (4R)-tert-butyldimethylsiloxy-2-(5-methoxycarbonylpentylthio)-2-cyclopenten-1-one (373 mg, 1 mmol), and isobutyric anhydride (448 μl), the same procedure was performed as in Example 1 to obtain methyl(11R,12S,13E,15S,17R)-9-isobutyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (466 mg, 65%).

Quellen und Nachweise

ORD-Eintrag
ord-8f870745fc5f496588a513ddc86e1f2b
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731452

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