Reaktion #2337995

ord-41c56c16592940d48acbb9fbd3856ba4

Reaktionsgleichung

CC(C)=O.ClCCl
CH2Cl2 acetone
C1CCNCC1
piperidine
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1
epothilone A
→
CCC(=O)C(C)(C)[C@@H](O)CC(=O)O
(3S)-4,4-Dimethyl-3-hydroxy-5-oxo-heptanoic acid

Edukte

CC(C)=O.ClCCl
CH2Cl2 acetone
C1CCNCC1
piperidine
—
titanium tetra-isopropylate
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1
epothilone A

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenAfter concentration in vacuo
  2. 2
    Sonstigethe product is purified by FC (200 g of silica gel, CH2Cl2→CH2Cl2/acetone=4:1)
  3. 3
    Sonstigegiving a colorless oil

Vorschrift

1 g (2.03 mmol) of epothilone A is dissolved in 168 mL of CH2Cl2. After adding 86 μl (0.88 mmol) of piperidine and 254 μl (0.88 mmol) of titanium tetra-isopropylate, the reaction solution is strirred for 16 h at RT. After concentration in vacuo, the product is purified by FC (200 g of silica gel, CH2Cl2→CH2Cl2/acetone=4:1) giving a colorless oil: Rf (CH2Cl2/acetone=85:15): 0.55; M+H=494.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07317100B2uspto-grants-2008_01