(2alpha,3xi,5beta,10beta,13alpha)-4,10-二乙酰氧基-13-{[(2R,3S)-3-(苯甲酰基氨基)-2-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-3-苯基丙酰基]氧基}-1-羟基-9-氧代-5,20-环氧紫杉-6,11-二烯-2-基苯甲酸酯 | 165065-02-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2alpha,3xi,5beta,10beta,13alpha)-4,10-二乙酰氧基-13-{[(2R,3S)-3-(苯甲酰基氨基)-2-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-3-苯基丙酰基]氧基}-1-羟基-9-氧代-5,20-环氧紫杉-6,11-二烯-2-基苯甲酸酯
• 中文别名: 2'-O-（叔丁基二甲基甲硅烷基）-6,7-脱氢紫杉醇
• 英文名称: 2'-O-(tert-butyldimethylsilyl)-6,7-dehydropaclitaxel
• 英文别名: 2'-(t-butyldimethylsilyl)-7-deoxy-Δ^6,7-paclitaxel；[(1S,2S,3R,4S,7R,10R,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadeca-8,13-dien-2-yl] benzoate
• CAS: 165065-02-1
• 化学式: C₅₃H₆₃NO₁₃Si
• 分子量: 950.168
• InChiKey: STDWDYDOHOANPV-BFKFGTFBSA-N

物化性质

• 溶解度：
  可溶于氯仿、二氯甲烷、乙酸乙酯、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  68
• 可旋转键数：
  17
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  190
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  (2alpha,3xi,5beta,10beta,13alpha)-4,10-二乙酰氧基-13-{[(2R,3S)-3-(苯甲酰基氨基)-2-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-3-苯基丙酰基]氧基}-1-羟基-9-氧代-5,20-环氧紫杉-6,11-二烯-2-基苯甲酸酯 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以50%的产率得到Δ^6,7-paclitaxel
  参考文献：
  名称：

  Synthesis and biological evaluation of paclitaxel analogs modified in ring C

  摘要：

  Both 7-deoxy-7 alpha-azidopaclitaxel (6) and 7-deoxy-Delta(6,7)-paclitaxel (4) can be prepared from paclitaxel-7-0-triflate (2b). Oxidation of 7-deoxy-Delta(6,7)-paclitaxel with dioxirane yields the epoxide 7, while oxidation with osmium tetroxide yields 6 alpha-hydroxy-7-epipaclitaxel (9), and acylation of this gives the 6 alpha-acyloxy-7-epipaclitaxel derivatives 11a-d. No compound was as effective at promoting tubulin assembly as paclitaxel, but most stabilized polymer as well as or better than paclitaxel. Compounds 4, 6, 7, 9, and 11d differed little from paclitaxel in their cytotoxicity for human Burkitt lymphoma CA46 cells.

  DOI：

  10.1016/0040-4039(95)00431-b
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 咪唑 、 三氟甲磺酸酐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2alpha,3xi,5beta,10beta,13alpha)-4,10-二乙酰氧基-13-{[(2R,3S)-3-(苯甲酰基氨基)-2-{[二甲基(2-甲基-2-丙基)硅烷基]氧基}-3-苯基丙酰基]氧基}-1-羟基-9-氧代-5,20-环氧紫杉-6,11-二烯-2-基苯甲酸酯
  参考文献：
  名称：

  Synthesis of novel taxol analogs and evaluation of their biological activities

  摘要：

  Two new taxol analogs 6 and 10 have been prepared from baccatin III (1) and taxol (7a), respectively. Like taxol, both compounds were found to promote microtubule formation and stabilization, although they were less active than taxol. Both 6 and 10 exhibited cytotoxicity against J774.2 cells; 6 was similar to 60-fold less active and 10 was similar to 15-fold less active. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00337-5

文献信息

• Paclitaxel analogs modified in ring C: Synthesis and biological evaluation
  作者：Xian Liang、David G.I. Kingston、Byron H. Long、Craig A. Fairchild、Kathy A. Johnston

  DOI：10.1016/s0040-4020(97)00074-4

  日期：1997.3

  Lead tetracetate oxidation of 6 alpha-hydroxy-7-epi-paclitaxel leads to C-nor-paclitaxel and C-seco-paclitaxel derivatives. Tetrapropylammonium permthenate (TPAP) oxidation of a 6 alpha-hydroxy-7-epi-paclitaxel derivative leads to a 6-formyl-C-nor-paclitaxel derivative. Reaction of a 6 alpha-O-trifluoromethanesulfonyl-7-epi-paclitaxel derivative with DMAP yields a 20-O-acetyl-4-deacetyl-5,6-dehydro-6-formyl-C-nor-paclitaxel derivative. C-nor-paclitaxel analogs are less active than paclitaxel. (C) 1997 Elsevier Science Ltd.
• An interesting c-ring contraction in paclitaxel (Taxol®)
  作者：Shu-Hui Chen、Stella Huang、Gregory P. Roth

  DOI：10.1016/0040-4039(95)01954-g

  日期：1995.12

  An interesting pinacol rearrangement involving 7-epi-6 alpha-tosylate/triflate-paclitaxel derivatives (6) and (10), with the formation of five-membered C-ring containing analogs (7) and (11), is described.
• Synthesis and biological activity of a novel C4–C6 bridged paclitaxel analog
  作者：Haiqing Yuan、David G.I. Kingston、Dan L. Sackett、Ernest Hamel

  DOI：10.1016/s0040-4020(99)00552-9

  日期：1999.8

  The novel paclitaxel analog 15 with a bridge between the C-4 and C-6 positions was synthesized and was found to be less active than paclitaxel in in vitro tubulin assembly and cytotoxicity assays. (C) 1999 Elsevier Science Ltd. All rights reserved.