2-[(6aR,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,9a-dihydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]ethynyl-trimethylsilane | 474409-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢噻吩类
• 英文名称: 2-[(6aR,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,9a-dihydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]ethynyl-trimethylsilane
• CAS: 474409-54-6
• 化学式: C₂₂H₄₂O₃SSi₃
• 分子量: 470.896
• InChiKey: BBJHIDOOPYNVDO-FCHUYYIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二(三甲硅氧基)嘧啶 、 2-[(6aR,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,9a-dihydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]ethynyl-trimethylsilane 在 N-碘代丁二酰亚胺 作用下， 生成
  参考文献：
  名称：

  4-Thiofuranoid Glycals: Versatile Synthons for Stereoselective Synthesis of 4′-Thionucleosides

  摘要：

  beta-anomers of 4'-thionucleosides have been synthesized stereoselectively, through PhSeCl- or N-iodosuccimide (NIS)-initiated electrophilic glycosidation to 3,5-O-(di-t-butylsilylene)-4-thiofuranoid glycal (1). This synthetic method has been applied to the synthesis of those analogues branched at the anomeric position using 1-C-carbon-substituted 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-4-thiofuranoid glycals (11-14) prepared based on lithiation of 10.

  DOI：

  10.1081/ncn-120022629
• 作为产物：
  描述：

  1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 碘 、 lithium diisopropyl amide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(6aR,9aS)-2,2,4,4-tetra(propan-2-yl)-6a,9a-dihydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]ethynyl-trimethylsilane
  参考文献：
  名称：

  立体选择性地从4-硫呋喃类化合物糖基进入1'- C-支链的4'-硫代核苷：合成4'-硫代angustmycin C

  摘要：

  已经开发了用于合成新型1' - C-碳取代的4'-硫代核苷的立体选择性合成方法。本方法包括以下步骤：（1）基于锂化制备1 - C-碳取代的4-硫呋喃类糖，和（2）NIS-或PhSeCl引发的对这些1-取代的糖的立体选择性糖苷化。该合成序列使我们能够合成抗肿瘤抗生素阿古霉素C的4'-硫代类似物。

  DOI：

  10.1016/s0040-4039(02)01131-0

文献信息

• 4-Thiofuranoid Glycals: Versatile Synthons for Stereoselective Synthesis of 4′-Thionucleosides
  作者：Kazuhiro Haraguchi、Haruhiko Takahashi、Hiromichi Tanaka

  DOI：10.1081/ncn-120022629

  日期：2003.10

  beta-anomers of 4'-thionucleosides have been synthesized stereoselectively, through PhSeCl- or N-iodosuccimide (NIS)-initiated electrophilic glycosidation to 3,5-O-(di-t-butylsilylene)-4-thiofuranoid glycal (1). This synthetic method has been applied to the synthesis of those analogues branched at the anomeric position using 1-C-carbon-substituted 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-4-thiofuranoid glycals (11-14) prepared based on lithiation of 10.
• Stereoselective entry to 1′-C-branched 4′-thionucleosides from 4-thiofuranoid glycal: synthesis of 4′-thioangustmycin C
  作者：Kazuhiro Haraguchi、Haruhiko Takahashi、Hiromichi Tanaka

  DOI：10.1016/s0040-4039(02)01131-0

  日期：2002.8

  1′-C-carbon-substituted 4′-thionucleosides has been developed. The present method consists of the following steps: (1) preparation of the 1-C-carbon-substituted 4-thiofuranoid glycals based on lithiation, and (2) NIS- or PhSeCl-initiated stereoselective glycosidation to these 1-substituted glycals. This synthetic sequence enabled us to synthesize the 4′-thio analogue of antitumor antibiotic angustmycin

  已经开发了用于合成新型1' - C-碳取代的4'-硫代核苷的立体选择性合成方法。本方法包括以下步骤：（1）基于锂化制备1 - C-碳取代的4-硫呋喃类糖，和（2）NIS-或PhSeCl引发的对这些1-取代的糖的立体选择性糖苷化。该合成序列使我们能够合成抗肿瘤抗生素阿古霉素C的4'-硫代类似物。