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Taxol and its analogue side chain synthesizing method

A synthetic method and analogue technology, applied in the field of synthesis of paclitaxel and its analogue side chains, can solve the problems that threaten the long-term persistence and regional distribution of Taxus plants

Inactive Publication Date: 2005-12-21
成都科杰高新技术发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the current extraction and separation methods, such a large supply will undoubtedly threaten the long-term persistence and regional distribution of Taxus plants. Therefore, it has become a current research hotspot to use various means to find alternative resources for paclitaxel and its analogues.

Method used

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  • Taxol and its analogue side chain synthesizing method
  • Taxol and its analogue side chain synthesizing method
  • Taxol and its analogue side chain synthesizing method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] (R)-benzaldehyde tert-butyl sulfenamide alkene 22a

[0065]

[0066] Colorless liquid, [α] 20 D -122°(c 1.0, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 ) δ 1.27 (s, 9H), 7.46-7.55 (m, 3H), 7.85-7.88 (m, 2H), 8.60 (s, 1H) ppm.

Embodiment 2

[0068] (R)-p-Chlorobenzaldehyde tert-butyl sulfenamide alkene 22b

[0069]

[0070] White solid, melting point 45-47°C. [α] 20 D -79°(c 2.19, CHCl 3 );. 1 H NMR (400MHz, CDCl 3 )δ1.26(s, 9H), 7.44(d, J=6.4Hz, 2H), 7.78(d, J=6.4Hz, 2H), 8.55(s, 1H); 13 C NMR (CDCl 3 ) delta 22.5, 57.8, 129.2, 130.4, 132.4, 138.5, 161.4 ppm.

Embodiment 3

[0072] (R)-Ortho-bromobenzaldehyde tert-butyl sulfenamide alkene 22c

[0073]

[0074] Colorless liquid, [α] 20 D -211.3° (c 1.23, CHCl 3 ); 1 H NMR (400MHz, CDCl 3 )δ8.94(s, 1H), 8.00(dd, J=7.6, 2.0Hz, 1H), 7.60(dd, J=7.6, 0.8Hz, 1H), 7.28-7.39(m, 2H), 1.24(s , 9H).

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Abstract

This invention has disclosed a kind of synthetic method to paclitaxol and side chain of its analogue. This invention using low-cost alpha- glycolic acid as raw material, the asymmetry addition reaction induced by chirality tertiary butyl sulfinamide as committed step, prepares paclitaxol and polyene paclitaxol side chain. The chemical product quotiety of key reaction is high, protecting group is easy to control and operate, synthesis process is short.

Description

technical field [0001] The invention relates to a method for synthesizing the side chains of paclitaxel and its analogs, in particular to a new method for synthesizing the side chains of paclitaxel and its analogs based on chiral tert-butyl sulfenamide niffervine. Background technique [0002] Paclitaxel, a diterpenoid compound with unique anticancer activity, was first extracted from the bark of Pacific yew (Taxus.brevifolia) by American chemists Wall and Wani in 1967. The drug entered Phase III clinical trials in 1990 and was approved by the US FDA at the end of 1992 for the treatment of ovarian and breast cancers that are ineffective against conventional chemotherapy. In 1995, my country Peking Union Medical College and Haikou Pharmaceutical Factory respectively obtained the approval number of Class II new drugs, becoming the second country in the world to produce paclitaxel and its injection. Due to its unique anticancer mechanism and broad-spectrum and efficient antica...

Claims

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Application Information

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IPC IPC(8): C07C313/06
CPCY02P20/55
Inventor 秦勇王印郭培良高建冯小明罗孝君章贤民
Owner 成都科杰高新技术发展有限公司
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