Reaktion #947584

ord-03f29817b26b40eb8864d19b462d7e2d

Reaktionsgleichung

C=CCC/C=C\C=C/CCCCCCCC[C@H]1CC[C@@H]([C@@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide A
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
( 2 )
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide B
C=CCC/C=C\C=C/CCCCCCCC[C@H]1CC[C@@H]([C@@H]2CC[C@@H](CC(=O)O)OO2)O1
( 1 )
C=CCC/C=C\C=C/CCCCCCCC[C@H]1CC[C@@H]([C@@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide A
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
( 2 )
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide B
→
C=CCC/C=C\C=C/CCCCCC[C@@H]1CC[C@@H]([C@@H]2CC[C@@H](CC(=O)OC)OO2)O1
stolonoxide A methyl ester

Edukte

C=CCC/C=C\C=C/CCCCCCCC[C@H]1CC[C@@H]([C@@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide A
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
( 2 )
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide B
C=CCC/C=C\C=C/CCCCCCCC[C@H]1CC[C@@H]([C@@H]2CC[C@@H](CC(=O)O)OO2)O1
( 1 )
C=CCC/C=C\C=C/CCCCCCCC[C@H]1CC[C@@H]([C@@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide A
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
( 2 )
C=CCCC/C=C/C=C\CCCCCCCC[C@H]1CC[C@@H]([C@H]2CC[C@@H](CC(=O)O)OO2)O1
stolonoxide B
—
stolonoxides

Reagenzien

Keine

Lösungsmittel

CCOCC
Et2O

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe solvent was removed under reduced pressure
  2. 2
    Sonstigethe reaction crude

Vorschrift

Methylation of the mixture of stolonoxides A (1) and B (2): Excess of CH2N2 was added to a solution of the mixture of stolonoxide A (1) and B (2) (22 mg) in Et2O (2 mL) at room temperature. After 1 h, the solvent was removed under reduced pressure and the reaction crude subjected to HPLC chromatography yielding stolonoxide A methyl ester (1b, 18 mg) and stolonoxide B methyl ester (2b, 2 mg).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07153885B2uspto-grants-2006_12