Ethane, 1-chloro-1-ethoxy- → (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine

HRID 1376931

Reaktionsgleichung

Reaktionsgleichung von HRID 1376931
[C:1]([NH:9][C@@H:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:11]([C:13]([OH:15])=[O:14])[OH:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:23]([O:25][CH2:26][CH3:27])[CH3:24]>>[C:1]([NH:9][C@@H:10]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C@H:11]([C:13]([O:15][CH:23]([O:25][CH2:26][CH3:27])[CH3:24])=[O:14])[OH:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

3

Edukt 2

HCID 23478Ethane, 1-chloro-1-ethoxy-HCID 2762289N-Benzoyl-3-phenylisoserine, (2R,3S)-

Produkt 1

HCID 68784626(2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine

Versuchsvorschrift

The N-benzoyl-(2R,3S)-3-phenyl-isoserine, as prepared in Example 34, is treated with 1-chloroethyl ethyl-ether in the presence of a tertiary amine to produce optically pure (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine (2). 7-tri-ethylsilyl baccatin III (1), as synthesized according to Denis et at. (J. Amer. Chem. Soc. 110:5417, 1988), is added to 6 equiv of optically pure (2R,3S)-N-benzoyl-O-(1-ethoxyethyl)-3-phenyl-isoserine (2), 6 equiv of di-2-pyridyl carbonate (DPC), and 2 equiv of 4-(dimethylamino) pyridine (DMAP) in toluene solution (0.02M). This mixture reacts at 73° C. for 100 hours to produce the C-2', C-7-protected taxol derivative (3).

Quellen und Nachweise

ORD-Eintrag
ord-0b456f04b6d84029830f0a4f4911399c
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663393

Verknüpfte Notizen

Wird geladen…