HCID 14988888, Verbindung → HCID 14988907, Verbindung

HRID 481325Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 481325
[CH3:1][O:2][CH:3]1[CH:10]([O:11][C:12]([N:14]2[CH2:19][CH2:18][S:17][CH2:16][CH2:15]2)=[O:13])[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]1[C:20]1([CH3:28])[CH:22]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[O:21]1.I([O-])(=O)(=O)=[O:30].[Na+]>O1CCOCC1.O.C(OCC)C>[CH3:1][O:2][CH:3]1[CH:10]([O:11][C:12]([N:14]2[CH2:19][CH2:18][S:17](=[O:30])[CH2:16][CH2:15]2)=[O:13])[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]1[C:20]1([CH3:28])[CH:22]([CH2:23][CH:24]=[C:25]([CH3:27])[CH3:26])[O:21]1

Komponenten

6

Edukt 2

HCID 14988888HCID 14988888, VerbindungHCID 23667635Sodium periodate

Produkt 1

HCID 14988907HCID 14988907, VerbindungAusbeute 59,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-(thiomorpholin-4-ylcarbonyloxy)-1-oxaspiro[2,5]octane (41 mg) in 1,4-dioxane (2 ml) and water (0.2 ml) was added sodium periodate (21 mg) at ambient temperature. After stirring at the same temperature for 18 hours, the reaction mixture was diluted with diethyl ether. The precipitates were filtered off by celite and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution by ethyl acetate) to yield 5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-(1-oxothiomorpholin-4-ylcarbonyloxy)-1-oxaspiro[2,5]octane (25 mg) as an oil.

Aufarbeitung

  1. filtrationThe precipitates were filtered off by celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel (elution by ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8b580a49f235462aa2b53859119698f8
Quelldatensatz
uspto-grants-1998_08
Patentnummer
US05789405

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