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Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)- → 3',4'-Anhydrovinblastine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2beta,3beta,4beta,5alpha,12beta,19alpha)- | HCID 16596 | — |
| 反応物 | (+)-Catharanthine | HCID 5458190 | — |
| 生成物 | 3',4'-Anhydrovinblastine | HCID 443324 | — |
反応手順
In J. Am. Chem. Soc./98:22/Oct. 27, 1976, Langlois et al describe a process in which the monomers catharanthine and vindoline are coupled to form AVLB. The coupling is performed using a peracid to generate first the N-oxide of catharanthine, followed by Polonovski-type fragmentation of the N-oxide initiated with addition of trifluoroacetic anhydride to form a dimer. A reducing agent such as sodium borohydride is then added to generate AVLB which can be isolated e.g. chromatographically.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05034320 |
| 出典データセット | uspto-grants-1991_07 |
| ORD ID | ord-e7abaf1b05c040e8a2584989826f2ee9 |
| 出典メモ | uspto-grants-1991_07 |