Paclitaxel → Taxane

HRID 2070215

반응식

[CH3:1][C:2]1[C@@H:19](OC([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:18][C@:14]2(O)[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4](OC(C)=O)[C:5]([C@@:7]1([CH3:58])[C@H:12]([C@@H:13]2OC([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=O)[C@:11]2(OC(C)=O)[CH2:51]O[C@@H:10]2[CH2:9][C@@H:8]1O)=O.CC1[C@@H]([O:82][C:83]([C@H:85]([OH:101])[C@@H:86]([NH:93]C(OC(C)(C)C)=O)C2C=CC=CC=2)=[O:84])C[C@]2(O)C(C)(C)C=1[C@@H](O)C([C@@]1(C)[C@H]([C@@H]2OC(C2C=CC=CC=2)=O)[C@]2(OC(C)=O)CO[C@@H]2C[C@@H]1O)=O.CC1[C@@H](OC([C@H](O)[C@@H](NC(C(C)C)=O)C2C=CC=CC=2)=O)C[C@]2(O)C(C)(C)C=1[C@@H](OC(C)=O)C([C@@]1(C)[C@H]([C@@H]2OC(C2C=CC=CC=2)=O)[C@]2(OC(C)=O)CO[C@@H]2C[C@@H]1O)=O>>[CH3:51][C@H:11]1[C@H:12]2[CH2:13][C@H:14]3[C:15]([CH3:16])([CH3:17])[C@@H:3]([CH2:4][CH2:5][C@:7]2([CH3:58])[CH2:8][CH2:9][CH2:10]1)[C@H:2]([CH3:1])[CH2:19][CH2:18]3.[C:45]1([NH:93][CH2:86][CH:85]([C:83]([OH:84])=[O:82])[OH:101])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

참가 물질

반응물 3

HCID 36314Paclitaxel

HCID 148124Docetaxel

HCID 9832370Canadensol

생성물 2

HCID 9548828Taxane

HCID 18363976Phenylisoserine

실험 절차

In brief, the present invention relates to an improved semi-synthetic process to produce a taxane intermediate, which can ultimately be used to produce taxane derivatives, such as paclitaxel, docetaxel and canadensol and its derivatives. In the process of the present invention, the protected taxane intermediate from which the taxane derivative can be derived is produced in a yield of over 65% of a single isomer by direct esterification of a protected taxane of formula (I) with a single isomeric open chain phenyl isoserine side chain. By using a single isomeric phenyl isoserine side chain, a single isomeric taxane intermediate is obtained at a yield of over 65%. This is substantially greater than the 40% yield of the process advanced by Denis et al in U.S. Pat. No. 4,924,011. In addition, by using the same hydroxyl protecting group to protect both the C-7 position and the 2′-position on the phenylisoserine side chain, simplifies and reduces the reaction route. These are all features which would be recognised as being advantageous in industrial scale up of the present process.

출처 및 근거

ORD 기록: ord-7cce0a54458f4d0e8b987c0a9612f6ec
출처 데이터셋: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US08299279B2

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