(2R,3S,4S)-8-Benzyloxy-2,3-dihydroxy-4-methyl-octanoic acid methyl ester | 190712-22-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4S)-8-Benzyloxy-2,3-dihydroxy-4-methyl-octanoic acid methyl ester
• 英文别名: methyl (2R,3S,4S)-2,3-dihydroxy-4-methyl-8-phenylmethoxyoctanoate
• CAS: 190712-22-2
• 化学式: C₁₇H₂₆O₅
• 分子量: 310.39
• InChiKey: PUKMSBZBJIQUJQ-CWRNSKLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-8-Benzyloxy-2,3-dihydroxy-4-methyl-octanoic acid methyl ester 在 锂硼氢 、 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 [(4S,5S)-5-((S)-5-Benzyloxy-1-methyl-pentyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol
  参考文献：
  名称：

  Sunthetic Studies of Microsclerodermins. A Stereoselective Synthesis of a Core Building Block for (2 S,3 R, 4 S,5 S,6 S, 11 E)-3-Amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic Acid (AMMTD)

  摘要：

  A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-aminod-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydoda. -11-enoic acid (2, AMMTD) has been efficiently synthesized using the sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a nitrone derivative as key steps. The 2-furyl group has been used as the carboxylsynthon. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00522-4
• 作为产物：
  描述：

  (S)-6-benzyloxy-2-methyl-1-hexanol 在 AD-mix-α 、 草酰氯 、 甲基磺酰胺 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 28.0h， 生成 (2R,3S,4S)-8-Benzyloxy-2,3-dihydroxy-4-methyl-octanoic acid methyl ester
  参考文献：
  名称：

  Sunthetic Studies of Microsclerodermins. A Stereoselective Synthesis of a Core Building Block for (2 S,3 R, 4 S,5 S,6 S, 11 E)-3-Amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic Acid (AMMTD)

  摘要：

  A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-aminod-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydoda. -11-enoic acid (2, AMMTD) has been efficiently synthesized using the sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a nitrone derivative as key steps. The 2-furyl group has been used as the carboxylsynthon. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00522-4

文献信息

• Sunthetic Studies of Microsclerodermins. A Stereoselective Synthesis of a Core Building Block for (2 S,3 R, 4 S,5 S,6 S, 11 E)-3-Amino-6-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydodec-11-enoic Acid (AMMTD)
  作者：Shigekazu Sasaki、Yasumasa Hamada、Takayuki Shioiri*

  DOI：10.1016/s0040-4039(97)00522-4

  日期：1997.4

  A core building block 3 for (2S,3R,4S,5S,6S,11E)-3-aminod-methyl-12-(4-methoxyphenyl)-2,4,5-trihydroxydoda. -11-enoic acid (2, AMMTD) has been efficiently synthesized using the sharpless asymmetric dihydroxylation and the Dondoni's furan addition to a nitrone derivative as key steps. The 2-furyl group has been used as the carboxylsynthon. (C) 1997 Elsevier Science Ltd.