1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-C-(quinolin-3-yl)-4-thio-D-erythro-pento-1-enitol | 1335287-23-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-C-(quinolin-3-yl)-4-thio-D-erythro-pento-1-enitol
• 英文别名: 3-[(4aR,7aS)-2,2-ditert-butyl-4a,7a-dihydro-4H-thieno[3,2-d][1,3,2]dioxasilin-6-yl]quinoline
• CAS: 1335287-23-4
• 化学式: C₂₂H₂₉NO₂SSi
• 分子量: 399.629
• InChiKey: XAVGYDNEPXBGAB-AZUAARDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-C-(quinolin-3-yl)-4-thio-D-erythro-pento-1-enitol 在 硼烷四氢呋喃络合物 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 生成 3-[3,5-O-(di-tert-butylsilylene)-4-thio-β-D-ribofuranosyl]quinoline
  参考文献：
  名称：

  An Access to the β-Anomer of 4′-Thio-C-ribonucleosides: Hydroboration of 1-C-Aryl- or 1-C-Heteroaryl-4-thiofuranoid Glycals and Its Regiochemical Outcome

  摘要：

  We have developed a novel method for the synthesis of the beta-anomer of 4'-thio-C-ribonucleosides from 3,5-O-(di-tert-butylsilylene)-4-thiofuranoid glycal. Palladium-catalyzed coupling of 1-tributylstannyl-4-thiofuranoid glycal with iodobenzene or a heteroaryl halide gave 1-C-phenyl- or 1-C-heteroaryl-glycals. Hydroboration of these glycals proceeded at the alpha-face, and subsequent alkaline hydrogen peroxide treatment of the resulting 2'-alpha-borane furnished the respective beta-anomer of 4'-thio-C-ribonucleosides. These results demonstrate that this synthetic method has a wider scope in terms of heterocyclic base structure. During this study, unexpected Markovnikov-oriented hydroboration has been observed to lead to the respective 1'-alpha-boranes. These 1'-boranes were converted into either the ring-opened structure or the 2'-deoxy derivatives depending upon their stability.

  DOI：

  10.1021/jo201100n
• 作为产物：
  描述：

  3-溴喹啉 、 1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-tributylstannyl-4-thio-D-erythro-pento-1-enitol 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以95%的产率得到1,4-anhydro-2-deoxy-3,5-O-(di-tert-butylsilylene)-1-C-(quinolin-3-yl)-4-thio-D-erythro-pento-1-enitol
  参考文献：
  名称：

  An Access to the β-Anomer of 4′-Thio-C-ribonucleosides: Hydroboration of 1-C-Aryl- or 1-C-Heteroaryl-4-thiofuranoid Glycals and Its Regiochemical Outcome

  摘要：

  We have developed a novel method for the synthesis of the beta-anomer of 4'-thio-C-ribonucleosides from 3,5-O-(di-tert-butylsilylene)-4-thiofuranoid glycal. Palladium-catalyzed coupling of 1-tributylstannyl-4-thiofuranoid glycal with iodobenzene or a heteroaryl halide gave 1-C-phenyl- or 1-C-heteroaryl-glycals. Hydroboration of these glycals proceeded at the alpha-face, and subsequent alkaline hydrogen peroxide treatment of the resulting 2'-alpha-borane furnished the respective beta-anomer of 4'-thio-C-ribonucleosides. These results demonstrate that this synthetic method has a wider scope in terms of heterocyclic base structure. During this study, unexpected Markovnikov-oriented hydroboration has been observed to lead to the respective 1'-alpha-boranes. These 1'-boranes were converted into either the ring-opened structure or the 2'-deoxy derivatives depending upon their stability.

  DOI：

  10.1021/jo201100n

文献信息

• An Access to the β-Anomer of 4′-Thio-C-ribonucleosides: Hydroboration of 1-<i>C</i>-Aryl- or 1-<i>C</i>-Heteroaryl-4-thiofuranoid Glycals and Its Regiochemical Outcome
  作者：Kazuhiro Haraguchi、Chikafumi Horii、Yuichi Yoshimura、Fumiko Ariga、Aya Tadokoro、Hiromichi Tanaka

  DOI：10.1021/jo201100n

  日期：2011.11.4

  We have developed a novel method for the synthesis of the beta-anomer of 4'-thio-C-ribonucleosides from 3,5-O-(di-tert-butylsilylene)-4-thiofuranoid glycal. Palladium-catalyzed coupling of 1-tributylstannyl-4-thiofuranoid glycal with iodobenzene or a heteroaryl halide gave 1-C-phenyl- or 1-C-heteroaryl-glycals. Hydroboration of these glycals proceeded at the alpha-face, and subsequent alkaline hydrogen peroxide treatment of the resulting 2'-alpha-borane furnished the respective beta-anomer of 4'-thio-C-ribonucleosides. These results demonstrate that this synthetic method has a wider scope in terms of heterocyclic base structure. During this study, unexpected Markovnikov-oriented hydroboration has been observed to lead to the respective 1'-alpha-boranes. These 1'-boranes were converted into either the ring-opened structure or the 2'-deoxy derivatives depending upon their stability.