(3R,4R)-4,6-di(tert-butyldimethylsilyloxy)-3-methylhexanenitrile | 473901-33-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,4R)-4,6-di(tert-butyldimethylsilyloxy)-3-methylhexanenitrile
• 英文别名: (3R,4R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methylhexanenitrile
• CAS: 473901-33-6
• 化学式: C₁₉H₄₁NO₂Si₂
• 分子量: 371.711
• InChiKey: HPAKLPLIQCUPPB-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4R)-4,6-di(tert-butyldimethylsilyloxy)-3-methylhexanenitrile 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 22.0h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-3-hydroxy-4-methyl-6-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-hexyl ester
  参考文献：
  名称：

  Stereostructure of a Novel Cytotoxic 18-Membered Macrolactone Antibiotic FD-891

  摘要：

  [GRAPHICS]The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations.

  DOI：

  10.1021/ol026518k
• 作为产物：
  描述：

  (3R,4R)-5-benzyloxy-1,3-di(tert-butyldimethylsilyloxy)-4-methylpentane 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 32.5h， 生成 (3R,4R)-4,6-di(tert-butyldimethylsilyloxy)-3-methylhexanenitrile
  参考文献：
  名称：

  Stereostructure of a Novel Cytotoxic 18-Membered Macrolactone Antibiotic FD-891

  摘要：

  [GRAPHICS]The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations.

  DOI：

  10.1021/ol026518k

文献信息

• Stereostructure of a Novel Cytotoxic 18-Membered Macrolactone Antibiotic FD-891
  作者：Tadashi Eguchi、Kayako Kobayashi、Hidehiro Uekusa、Yuji Ohashi、Kazutoshi Mizoue、Yoshitaka Matsushima、Katsumi Kakinuma

  DOI：10.1021/ol026518k

  日期：2002.10.1

  [GRAPHICS]The absolute stereochemistry of FD-891, a novel cytotoxic 18-membered macrolactone antibiotic, was determined by a synthetic approach as well as X-ray diffraction of degradative derivatives. The absolute configuration of FD-891 turned out to be as shown above. The stable conformer of FD-891 was also discussed with respect to biological activity by comparison with the structurally related concanamycin A on the bases of molecular mechanics calculations.