Tetrahydrofuran → 1alpha-(tert-butyldimethylsilyloxy)-3beta-hydroxy-20(S)-{(Z)-4-ethyl-4-triethylsilyloxy-2-hexenylthio}pregna-5,7,16-triene

HRID 635025Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 635025
[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][C:24](OC2C=CC=CC=2)=O)[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].BrC/[CH:43]=[CH:44]\[C:45]([CH2:56][CH3:57])([O:48][Si:49]([CH2:54][CH3:55])([CH2:52][CH3:53])[CH2:50][CH3:51])[CH2:46][CH3:47].O1CCCC1.[OH-].[K+]>CO>[Si:1]([O:8][C@@H:9]1[C@@:37]2([CH3:38])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:36]2[CH2:35][CH2:34][C@@:33]2([CH3:39])[C@H:17]3[CH2:18][CH:19]=[C:20]2[C@@H:21]([S:23][CH2:24]/[CH:43]=[CH:44]\[C:45]([CH2:56][CH3:57])([O:48][Si:49]([CH2:52][CH3:53])([CH2:54][CH3:55])[CH2:50][CH3:51])[CH2:46][CH3:47])[CH3:22])[CH2:12][C@@H:11]([OH:40])[CH2:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 12019512HCID 12019512, VerbindungHCID 86584696(Z)-1-bromo-4-ethyl-4-triethylsilyloxy-2-hexene

Produkt 1

HCID 700086081alpha-(tert-butyldimethylsilyloxy)-3beta-hydroxy-20(S)-{(Z)-4-ethyl-4-triethylsilyloxy-2-hexenylthio}pregna-5,7,16-trieneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Under the same conditions as in Example 3, 1α-(tert-butyldimethylsilyloxy)-3β-hydroxy-20(S)-phenoxycarbonylthio-pregna-5,7,16-triene (33.0 mg, 0.0568 mmol), (Z)-1-bromo-4-ethyl-4-triethylsilyloxy-2-hexene (91.0 mg, 0.284 mmol), tetrahydrofuran (0.5 ml) and 1M KOH solution in methanol (0.5 ml) were reacted and worked up, and then the residue was purified by preparative thin layer chromatography (0.5 mm×1, hexane:ethyl acetate=2:1, developed once) to give the title compound as a pale yellow oil (23.8 mg, 60%).

Aufarbeitung

  1. customthe residue was purified by preparative thin layer chromatography (0.5 mm×1, hexane

Quellen und Nachweise

ORD-Eintrag
ord-64f7b0c793574744a17af495f47d5d87
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184398B2

Notizen zur Reaktion

Wird geladen…