Reaktion #482088

ord-969db5e5e9ed42fba31e2fb38773cc7a

Reaktionsgleichung

C/C1=C/C[C@@H](/C(C)=C/c2csc(C)n2)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC1
desoxyepothilone B
CC1(C)OO1
dimethyidioxirane
→
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1
( 2 )
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1
Epothilone B

Edukte

C/C1=C/C[C@@H](/C(C)=C/c2csc(C)n2)OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@@H](O)[C@@H](C)CCC1
desoxyepothilone B
CC1(C)OO1
dimethyidioxirane

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Temperatur
-50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe dimethyldioxirane and solvent were removed by a stream of N2
  2. 2
    SonstigeThe residue was purified by flash column chromatography (hexanes/ethyl acetate, 1:1)

Vorschrift

To a solution of desoxyepothilone B (0.0022 g, 0.0041 mmol) in CH2Cl2 (0.25 mL) at −50° C. was added dimethyidioxirane (0.1 mL, 0.0095 mmol) dropwise. The resulting solution was stirred at −50° C. for 1 h. The dimethyldioxirane and solvent were removed by a stream of N2. The residue was purified by flash column chromatography (hexanes/ethyl acetate, 1:1) gave 0.0015 g (70%) of epothiolone B (2) as a pale yellow oil which was identical with an authentic sample in 1H NMR, IR, mass spectrum, and [α]D.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06603023B2uspto-grants-2003_08