(R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid | 887927-18-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid
• 英文别名: (3R)-3-[tert-butyl(diphenyl)silyl]oxy-4-[(2S,6R)-6-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]oxan-2-yl]butanoic acid
• CAS: 887927-18-6
• 化学式: C₃₁H₄₄O₆Si
• 分子量: 540.772
• InChiKey: RGUSGJDQXFMVJY-BKKFENPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Potent, PKC Selective, B-Ring Analog of Bryostatin

  摘要：

  The first member of a new class of five-membered B-ring analogs of bryostatin has been synthesized and tested for its ability to bind and translocate protein kinase C (PKC). This synthesis extends the utility of our previously introduced macrotransacetalization strategy to the formation of five-membered dioxolane B-ring analogs. This analog exhibits potent, single-digit nanomolar affinity to PKC and selectively translocates novel PKC isozymes.

  DOI：

  10.1021/ol060457z
• 作为产物：
  描述：

  tert-butyl-diphenyl-[(2S)-4-phenylmethoxy-1-[(2S,6R)-6-prop-2-enyloxan-2-yl]butan-2-yl]oxysilane 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 palladium dihydroxide 、 potassium hexacyanoferrate(III) sodium hypochlorite 、 sodium chlorite 、 phosphate buffer 、 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 potassium dioxotetrahydroxoosmate(VI) 、 氢气 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 4.0~45.0 ℃ 、1.24 MPa 条件下， 反应 66.5h， 生成 (R)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butyric acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of a Potent, PKC Selective, B-Ring Analog of Bryostatin

  摘要：

  The first member of a new class of five-membered B-ring analogs of bryostatin has been synthesized and tested for its ability to bind and translocate protein kinase C (PKC). This synthesis extends the utility of our previously introduced macrotransacetalization strategy to the formation of five-membered dioxolane B-ring analogs. This analog exhibits potent, single-digit nanomolar affinity to PKC and selectively translocates novel PKC isozymes.

  DOI：

  10.1021/ol060457z

文献信息

• [EN] BRYOSTATIN ANALOGUES, SYNTHETIC METHODS AND USES<br/>[FR] ANALOGUES DE LA BRYOSTATINE, PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2009052507A1

  公开（公告）日：2009-04-23

  Biologically active compounds related to the bryostatin family of compounds, having simplified spacer domains and/or improved recognition domains are disclosed, including methods of preparing and utilizing the same.

  与拟静脉注射药物bryostatin家族相关的生物活性化合物，具有简化的间隔区域和/或改进的识别区域，包括其制备和利用方法。