(3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-(methoxymethoxy)-3-(phenylmethoxymethyl)-2-benzofuran-1-one | 1170721-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-(methoxymethoxy)-3-(phenylmethoxymethyl)-2-benzofuran-1-one
• CAS: 1170721-98-8
• 化学式: C₂₅H₃₄O₆Si
• 分子量: 458.627
• InChiKey: JHQAOWMFUSCZEQ-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-(methoxymethoxy)-3-(phenylmethoxymethyl)-2-benzofuran-1-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(3R)-3-((benzyloxy)methyl)-3-(((tert-butyldimethylsilyl)oxy)methyl)-7-(methoxymethoxy)-1,3-dihydroisobenzofuran-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators

  摘要：

  Efficient enantio-selective synthesis of conformationally constrained diacylglycerol analogues, 7-substituted isobenzofuranone derivatives, originally developed by us as PKC alpha ligands, was achieved by asymmetric dihydroxylation and gamma-lactone formation via ortho-lithiation and carboxylation. A series of derivatives having straight and/or branched side chains were synthesized and evaluated, and low-nanomolar-concentration affinity ligands and highly potent PKC alpha activators were found among them. These potent ligands induced phenotypic change of K562 cells, which is characteristic of PKC activators. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.069
• 作为产物：
  描述：

  二氧化碳 、 (R)-1-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-2-(3-(methoxymethoxy)phenyl)propan-2-ol 在 正丁基锂 作用下， 以 正己烷 为溶剂， 以80%的产率得到(3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-(methoxymethoxy)-3-(phenylmethoxymethyl)-2-benzofuran-1-one
  参考文献：
  名称：

  Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators

  摘要：

  Efficient enantio-selective synthesis of conformationally constrained diacylglycerol analogues, 7-substituted isobenzofuranone derivatives, originally developed by us as PKC alpha ligands, was achieved by asymmetric dihydroxylation and gamma-lactone formation via ortho-lithiation and carboxylation. A series of derivatives having straight and/or branched side chains were synthesized and evaluated, and low-nanomolar-concentration affinity ligands and highly potent PKC alpha activators were found among them. These potent ligands induced phenotypic change of K562 cells, which is characteristic of PKC activators. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.069

文献信息

• Asymmetric synthesis of isobenzofuranone derivatives and their unique character as protein kinase Cα (PKCα) activators
  作者：Go Hirai、Yosuke Ogoshi、Megumi Ohkubo、Yuki Tamura、Toru Watanabe、Tadashi Shimizu、Mikiko Sodeoka

  DOI：10.1016/j.tetlet.2009.03.069

  日期：2009.7

  Efficient enantio-selective synthesis of conformationally constrained diacylglycerol analogues, 7-substituted isobenzofuranone derivatives, originally developed by us as PKC alpha ligands, was achieved by asymmetric dihydroxylation and gamma-lactone formation via ortho-lithiation and carboxylation. A series of derivatives having straight and/or branched side chains were synthesized and evaluated, and low-nanomolar-concentration affinity ligands and highly potent PKC alpha activators were found among them. These potent ligands induced phenotypic change of K562 cells, which is characteristic of PKC activators. (C) 2009 Elsevier Ltd. All rights reserved.