FIELD: chemistry.
SUBSTANCE: invention relates to a method of obtaining 10-deacetylbaccatine III with purity of over 99%, which does not contain 10-deacetyl-2-debenzoyl-2-pentenoylbaccatine III. The disclosed method includes: a) treating crude 10-deacetylbaccatine III with an activated derivative of trichloroacetic acid; b) carrying out chromatography on silica gel and elution of 7,10-bis-trichloroacetyl-10-deacetylbaccatine III with dichloromethane or a dichloromethane/ethylacetate mixture; and c) treatment of 10-deacetyl-7,10-bis-trichloroacetylbaccatine III with an alkali followed by crystallisation. The invention also relates to production of paclitaxel, which involves production of 10-deacetylbaccatine III using the disclosed method and its subsequent conversion to N-debenzoylpaclitaxel with its subsequent benzoylation.
EFFECT: convenient semi-synthesis of anti-tumour agents with a taxane backbone, which enables to avoid laborious methods of removing corresponding 2-debenzoyl-2-pentenoyl analogues.
7 cl, 1 tbl, 3 ex
| Title | Year | Author | Number |
|---|---|---|---|
| SEMISYNTHETIC METHOD OF PRODUCING 10-DEACETYL-N-DEBENZOYLPACLITAXEL | 2005 |
|
RU2384578C2 |
| METHOD OF PRODUCING DOCETAXEL | 2005 |
|
RU2510395C2 |
| METHOD FOR PREPARING PACLITAXEL | 2001 |
|
RU2276147C2 |
| DERIVATIVES OF 10-DEACETYLBACCATIN-III AND 10-DEACETYL-14β- HYDROXYBACCATIN-III, METHOD OF THEIR SYNTHESIS, INTERMEDIATE COMPOUNDS AND PHARMACEUTICAL COMPOSITION | 1996 |
|
RU2152936C1 |
| 10-DIACETYL-14-BETA-HYDROXYBACCATIN III DERIVATIVES, METHOD OF PREPARING THEREOF, AND COMPOSITIONS COMPRISING SAID COMPOUNDS | 1996 |
|
RU2161615C2 |
| METHOD FOR PREPARING TAXANES AND INTERMEDIATE COMPOUND FOR THEIR PREPARING | 2000 |
|
RU2233276C2 |
| METHOD FOR PREPARING DERIVATIVES OF BACCATIN III | 2001 |
|
RU2264394C2 |
| METHOD FOR PREPARING TAXANE DERIVATIVES | 2001 |
|
RU2275365C2 |
| 10-DEACETOXYTAXOL OR ITS DERIVATIVES | 1992 |
|
RU2114836C1 |
| C-4 CARBONATE-COMPRISING TAXANES | 2000 |
|
RU2243223C2 |
