2'-O-TBDMS-7-O-TES-9-α-OH-9-desoxo-10-epi-paclitaxel | 162664-57-5

• 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
• 英文名称: 2'-O-TBDMS-7-O-TES-9-α-OH-9-desoxo-10-epi-paclitaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10R,11R,12S,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-[tert-butyl(dimethyl)silyl]oxy-3-phenylpropanoyl]oxy-1,11-dihydroxy-10,14,17,17-tetramethyl-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 162664-57-5
• 化学式: C₅₉H₈₁NO₁₄Si₂
• 分子量: 1084.46
• InChiKey: PSDNNYNWEINTTM-HNFBENMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.59
• 重原子数：
  76
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  202
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2'-O-TBDMS-7-O-TES-9-α-OH-9-desoxo-10-epi-paclitaxel 在 氢氟酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.83h， 生成 2'-O-TBDMS-9-α-OH-9-desoxo-10-epipaclitaxel
  参考文献：
  名称：

  WO2008/106621

  摘要：

  公开号：
• 作为产物：
  描述：

  2'-TBS-10-deacetyl-7-TES-10α-hydroxypaclitaxel 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2'-O-TBDMS-7-O-TES-9-α-OH-9-desoxo-10-epi-paclitaxel
  参考文献：
  名称：

  The Chemistry of the Taxane Diterpene:  Stereoselective Reductions of Taxanes

  摘要：

  Stereoselective reductions of taxanes are detailed. Chelation-controlled reductions employing SmI2 are described for the stereoselective reduction of the 9-keto functionality of the diterpene moiety of several taxanes. In all cases the 9 beta-hydroxy stereochemistry was obtained exclusively. In addition to C9 reduction, partial C10-deoxygenation via beta-elimination was observed. Lower reaction temperatures favored the reduction pathway without beta-elimination. Acetic acid as the proton source gave higher yields and cleaner reaction products. This chemistry provided access to taxanes with 9 beta-hydroxy, 10 beta-hydroxy stereochemistry. Evidence is presented, suggesting that chelation of samarium with the 7 beta-hydroxyl group is required for the reduction of the C9 ketone moiety. The synthesis of paclitaxel analogues, possessing the 9 alpha-hydroxy, 10 alpha-hydroxy stereochemistry was also achieved. Reduction of the 10-ketone group of 10-oxopaclitaxel employing NaBH4 produced 10-deacetyl-10-epipaclitaxel stereoselectively. Using an excess of NaBH4 in this reaction gave exclusively the 9 alpha-hydroxy, 10 alpha-hydroxy paclitaxel analogue.

  DOI：

  10.1021/jo981194s

文献信息

• Syntheses of novel C-9 and C-10 modified bioactive taxanes
  作者：Apurba Datta、David G. Vander Velde、Gunda I. Georg、Richard H. Himes

  DOI：10.1016/0040-4039(95)00208-t

  日期：1995.3

  A method has been developed for the syntheses of hitherto unreported C-9 and C-10 modified taxanes. These analogs demonstrated excellent to good cytotoxicity against B 16 melanoma cells.

  已经开发了一种用于合成迄今未报道的C-9和C-10修饰的紫杉烷的方法。这些类似物对B 16黑色素瘤细胞表现出优异的细胞毒性。
• Biologically Active Taxane Analogs and Methods of Treatment
  申请人：Lamb Rodger

  公开号：US20080207743A1

  公开（公告）日：2008-08-28

  The present application relates to new taxane analogs, pharmaceutical compositions comprising such analogs and methods of treating cancer comprising such compositions. The compounds according to the present application have the general formula: wherein R 1 and R 2 are each selected from H, alkyl, alkenyl or aryl; R 3 is hydroxyl or OP 1 ; R 4 is OH or R 7 COO; R 7 is alkyl, alkenyl or aryl, R 8 and R 9 are each independently selected from H, alkyl or alkenyl. The compounds of the present application may particularly be 9,10-α,α-OH taxane analogs that are formed by a process starting with a standard taxane as the starting compound.

  本申请涉及新的紫杉醇类似物，包括这种类似物的药物组合物以及包括这种组合物的治疗癌症的方法。根据本申请的化合物具有一般公式：其中R1和R2分别选自H、烷基、烯基或芳基；R3是羟基或OP1；R4是OH或R7COO；R7是烷基、烯基或芳基，R8和R9分别独立选自H、烷基或烯基。本申请的化合物可能特别是通过以标准紫杉醇作为起始化合物开始的过程形成的9,10-α,α-OH紫杉醇类似物。
• [EN] 9,10-alpha,alpha-OH-TAXANE ANALOGS AND METHODS FOR PRODUCTION THEREOF<br/>[FR] ANALOGUES DE 9,10-<supplemental>20050714</supplemental>US5635531ACHEN SHU-HUI [US]19970603XX
  申请人：TAPESTRY PHARMACEUTICALS INC

  公开号：WO2005030150A3

  公开（公告）日：2005-07-14
• WO2008/121476
  申请人：——

  公开号：——

  公开（公告）日：——