5-(((5R)-5-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-5-((triethylsilyl)oxy)pentan-2-yl)thio)-1-phenyl-1H-tetrazole | 1514894-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(((5R)-5-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-5-((triethylsilyl)oxy)pentan-2-yl)thio)-1-phenyl-1H-tetrazole
• CAS: 1514894-29-1
• 化学式: C₃₂H₅₈N₄O₃SSi₂
• 分子量: 635.075
• InChiKey: RJPRVLMKPBZVMX-DTTGCUBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.05
• 重原子数：
  42.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  71.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-(((5R)-5-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-5-((triethylsilyl)oxy)pentan-2-yl)thio)-1-phenyl-1H-tetrazole 在 sodium hexamethyldisilazane 、 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.17h， 生成 (4-((R,E)-3-methyl-6-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-6-((triethylsilyl)oxy)hex-2-en-1-yl)-2-nitro-1H-pyrrol-1-yl)methyl benzoate
  参考文献：
  名称：

  Total Synthesis of Heronapyrrole C

  摘要：

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.

  DOI：

  10.1021/ol403246j
• 作为产物：
  描述：

  triethyl((2-((2S,5S)-5-methyl-5-((R)-1-((triethylsilyl)oxy)pent-4-en-1-yl)tetrahydrofuran-2-yl)propan-2-yl)oxy)silane 在 偶氮二甲酸二异丙酯 、 mercury(II) diacetate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 25.5h， 生成 5-(((5R)-5-((2S,5S)-2-methyl-5-(2-((triethylsilyl)oxy)propan-2-yl)tetrahydrofuran-2-yl)-5-((triethylsilyl)oxy)pentan-2-yl)thio)-1-phenyl-1H-tetrazole
  参考文献：
  名称：

  Total Synthesis of Heronapyrrole C

  摘要：

  A flexible total synthesis of the 2-nitropyrrole-derived marine natural product, (+)-heronapyrrole C, is reported. The approach is based on regioselective access to key building blocks containing the rare 4-substituted 2-nitropyrrole motif. Sharp less asymmetric epoxidation and dihydroxylation and a Shi epoxidation were used to introduce the five stereogenic centers of the bis-THF-diol side chain. The N-benzoyloxymethyl (Boz) protecting group was crucial for functionalization of the 2-nitropyrrole moiety and enabling final deprotection under mild conditions.

  DOI：

  10.1021/ol403246j