(S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butan-1-ol | 887927-17-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butan-1-ol
• 英文别名: (3S)-3-[tert-butyl(diphenyl)silyl]oxy-4-[(2S,6R)-6-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]oxan-2-yl]butan-1-ol
• CAS: 887927-17-5
• 化学式: C₃₁H₄₆O₅Si
• 分子量: 526.789
• InChiKey: SXZBACMRZQJWCA-YYGZZXRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butan-1-ol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl sodium hypochlorite 、 sodium chlorite 、 phosphate buffer 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 以97%的产率得到(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
• 作为产物：
  描述：

  6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one 在 palladium dihydroxide 、 potassium hexacyanoferrate(III) 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 四氢呋喃 、 乙醚 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， -78.0~25.0 ℃ 、1.24 MPa 条件下， 反应 65.5h， 生成 (S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-[(2S,6R)-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-yl]-butan-1-ol
  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

• Design, Synthesis, and Biological Evaluation of a Potent, PKC Selective, B-Ring Analog of Bryostatin
  作者：Paul A. Wender、Vishal A. Verma

  DOI：10.1021/ol060457z

  日期：2006.4.1

  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.