반응 #2337995

ord-41c56c16592940d48acbb9fbd3856ba4

반응 방정식

CH2Cl2 acetone

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

→

(3S)-4,4-Dimethyl-3-hydroxy-5-oxo-heptanoic acid

반응물

CH2Cl2 acetone

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

시약

없음

용매

CH2Cl2

반응 조건

상세 조건

See reaction.notes.procedure_details.

후처리

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

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07317100B2uspto-grants-2008_01