tert-butyl-diphenyl-[(2S)-4-phenylmethoxy-1-[(2S,6R)-6-prop-2-enyloxan-2-yl]butan-2-yl]oxysilane | 887927-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl-diphenyl-[(2S)-4-phenylmethoxy-1-[(2S,6R)-6-prop-2-enyloxan-2-yl]butan-2-yl]oxysilane
• CAS: 887927-14-2
• 化学式: C₃₅H₄₆O₃Si
• 分子量: 542.834
• InChiKey: BNTSVCSFUAAZEI-CPCREDONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.44
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 、 三乙胺 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 4.0~45.0 ℃ 、1.24 MPa 条件下， 反应 71.5h， 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：

  6-[4-benzyloxy-2-(tert-butyldiphenylsilanyloxy)-butyl]-tetrahydropyran-2-one 、 烯丙基溴化镁 在 2-[[三(羟甲基)甲基]氨基]乙磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 以55%的产率得到tert-butyl-diphenyl-[(2S)-4-phenylmethoxy-1-[(2S,6R)-6-prop-2-enyloxan-2-yl]butan-2-yl]oxysilane
  参考文献：
  名称：

  Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues

  摘要：

  The design, synthesis, and biological evaluation of a novel class of C13-diversified bryostatin analogues are described. An innovative and general strategy based on a Prins macrocyclization-nucleophilic trapping cascade was used to achieve late-stage diversification. In vitro analysis of selected library members revealed that modification at the C13 position of the bryostatin scaffold can be used as a diversification handle to regulate biological activity.

  DOI：

  10.1055/s-0033-1338860

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.
• Lead Diversification through a Prins-Driven Macrocyclization Strategy: Application to C13-Diversified Bryostatin Analogues
  作者：Paul Wender、Kelvin Billingsley

  DOI：10.1055/s-0033-1338860

  日期：——

  The design, synthesis, and biological evaluation of a novel class of C13-diversified bryostatin analogues are described. An innovative and general strategy based on a Prins macrocyclization-nucleophilic trapping cascade was used to achieve late-stage diversification. In vitro analysis of selected library members revealed that modification at the C13 position of the bryostatin scaffold can be used as a diversification handle to regulate biological activity.