反応 #1150687

ord-b50ac8be2b794aad9b00b9a2ba821d71

反応方程式

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
dimethyldioxirane
→
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

反応物

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
dimethyldioxirane

試薬

なし

溶媒

ClCCl
CH2Cl2

反応条件

温度
-50°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

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

実験手順

To a solution of desoxyepothilone B (0.0022 g, 0.0041 mmol) in CH2Cl2 (0.25 mL) at −50° C. was added dimethyldioxirane (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.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US06965034B2uspto-grants-2005_11