Paclitaxel → Baccatin Iii

HRID 1590327

반응식

C/C=C(/C(N[C@H]([C@@H](O)C([O:18][C@@H:19]1[C:40]([CH3:41])=[C:39]2[C:42]([CH3:44])([CH3:43])[C@:21]([OH:59])([C@@H:22]([O:50][C:51]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)=[O:52])[C@@H:23]3[C@:28]4([O:31][C:32]([CH3:34])=[O:33])[CH2:29][O:30][C@@H:27]4[CH2:26][C@H:25]([OH:35])[C@@:24]3([CH3:49])[C:36]([C@@H:38]2[O:45][C:46]([CH3:48])=[O:47])=[O:37])[CH2:20]1)=O)C1C=CC=CC=1)=O)\C.CC1[C@@H](OC([C@H](O)[C@@H](NC(C2C=CC=CC=2)=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>>[CH3:41][C:40]1[C@@H:19]([OH:18])[CH2:20][C@:21]2([OH:59])[C:42]([CH3:43])([CH3:44])[C:39]=1[C@@H:38]([O:45][C:46]([CH3:48])=[O:47])[C:36]([C@@:24]1([CH3:49])[C@H:23]([C@@H:22]2[O:50][C:51]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)=[O:52])[C@:28]2([O:31][C:32]([CH3:34])=[O:33])[CH2:29][O:30][C@@H:27]2[CH2:26][C@@H:25]1[OH:35])=[O:37]

참가 물질

반응물 2

HCID 36314Paclitaxel

HCID 6436208Cephalomannine

생성물 1

HCID 65366Baccatin Iii

실험 절차

In the third embodiment, the addition of 10% tin chloride (based on the taxol in the starting material) to tetrabutylammonium borohydride in dichloromethane at 0° C. for one hour resulted in a 121.7% yield of Baccatin III. It would appear material other then just the cephalomannine and taxol in the starting material was cleaved to produce Baccatin III. It is hypothesized that certain taxol compounds may be bound to sugars and other biological material and that these may have been converted to Baccatin III in this process.

출처 및 근거

ORD 기록: ord-f981d4a919ec4c9b9365aa86304ae260
출처 데이터셋: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05202448

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