7-O-<<(trimethylsilyl)ethoxy>methyl>zaragozic acid A tris<2-(trimethylsilyl)ethyl ester> | 145294-71-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 7-O-<<(trimethylsilyl)ethoxy>methyl>zaragozic acid A tris<2-(trimethylsilyl)ethyl ester>
• 英文别名: 7-O-{[(trimethylsilyl)ethoxy]methyl}zaragozic acid A tris[2-(trimethylsilyl)ethyl ester]
• CAS: 145294-71-9
• 化学式: C₅₆H₉₆O₁₅Si₄
• 分子量: 1121.71
• InChiKey: UZELYAJAWFOJTF-KPORLZHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.61
• 重原子数：
  75.0
• 可旋转键数：
  32.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  188.65
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  7-O-<<(trimethylsilyl)ethoxy>methyl>zaragozic acid A tris<2-(trimethylsilyl)ethyl ester> 在 titanium(IV) tetraethanolate 、 2-(三甲硅基)乙醇 作用下， 反应 24.0h， 以66%的产率得到tris(2-trimethylsilylethyl) (1S,3S,4S,5R,6R,7R)-4,6-dihydroxy-1-[(4S,5R)-4-hydroxy-5-methyl-3-methylidene-6-phenylhexyl]-7-(2-trimethylsilylethoxymethoxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate
  参考文献：
  名称：

  Zaragozic acid A, a potent inhibitor of squalene synthase: initial chemistry and absolute stereochemistry

  摘要：

  Chemical studies on the highly potent squalene synthase inhibitor zaragozic acid A (1) have led to the determination of the total absolute stereochemistry of the molecule as shown in Figure 3 and to the feasibility of selectively manipulating the carboxyl and ester groups of the molecule. The absolute stereochemistry of the central core of 1 was established based on CD measurements on the bis(4-bromobenzoate) 8. The configuration of the methyl group in the C1 alkyl side chain was deduced by degrading 1 to (R)-(-)-2-methyl-3-phenylpropanoic acid, while the configuration of the adjacent acetoxy group was established from H-1 NMR considerations of the (R)- and (S)-O-methyl mandelates 14 and 15. Single-crystal X-ray diffraction data on two crystalline derivatives (16 and 17) not only led to clarification of the asymmetric centers in the 4,6-dimethyl-2-octenoyl side chain but also afforded independent structural confirmation of the nature of the chemical and biological heart of zaragozic acid A.

  DOI：

  10.1021/jo00052a032
• 作为产物：
  描述：

  O-<2-(trimethylsilyl)ethyl>-N,N'-diisopropylisourea 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 40.0h， 生成 7-O-<<(trimethylsilyl)ethoxy>methyl>zaragozic acid A tris<2-(trimethylsilyl)ethyl ester>
  参考文献：
  名称：

  Zaragozic acid A, a potent inhibitor of squalene synthase: initial chemistry and absolute stereochemistry

  摘要：

  Chemical studies on the highly potent squalene synthase inhibitor zaragozic acid A (1) have led to the determination of the total absolute stereochemistry of the molecule as shown in Figure 3 and to the feasibility of selectively manipulating the carboxyl and ester groups of the molecule. The absolute stereochemistry of the central core of 1 was established based on CD measurements on the bis(4-bromobenzoate) 8. The configuration of the methyl group in the C1 alkyl side chain was deduced by degrading 1 to (R)-(-)-2-methyl-3-phenylpropanoic acid, while the configuration of the adjacent acetoxy group was established from H-1 NMR considerations of the (R)- and (S)-O-methyl mandelates 14 and 15. Single-crystal X-ray diffraction data on two crystalline derivatives (16 and 17) not only led to clarification of the asymmetric centers in the 4,6-dimethyl-2-octenoyl side chain but also afforded independent structural confirmation of the nature of the chemical and biological heart of zaragozic acid A.

  DOI：

  10.1021/jo00052a032