Methanesulfonic acid (2R,3R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentyl ester | 473901-40-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Methanesulfonic acid (2R,3R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentyl ester
• CAS: 473901-40-5
• 化学式: C₁₉H₄₄O₅SSi₂
• 分子量: 440.792
• InChiKey: GKOKXUBPIVFHDA-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (2R,3R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentyl ester 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 、 二甲基亚砜 、 甲苯 为溶剂， 反应 34.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3R,4R)-3-hydroxy-4-methyl-6-((R)-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 为溶剂， 反应 20.5h， 生成 Methanesulfonic acid (2R,3R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pentyl 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