1-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(1S)-heptan-1-ol | 143707-07-7

• 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: 1-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(1S)-heptan-1-ol
• 英文别名: (2S,3S)-1,2-O-isopropylidene-1,2,3-nonanetriol；(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]heptan-1-ol
• CAS: 143707-07-7
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: UPOFGGRXXJHMDD-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(1S)-heptan-1-ol 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 、 sodium azide 、 三正丁胺 、 氨 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 戊醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 152.75h， 生成 9-(RS)-(1,2-Dihydroxy-3-nonyl)adenine
  参考文献：
  名称：

  Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine

  摘要：

  The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were Cl'- and nor-Cl'-(+)-EHNA derivatives. When tested with calf spleen ADA, Cl'-OH- and nor-Cl'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-Cl' derivatives.

  DOI：

  10.1021/jm00100a025
• 作为产物：
  描述：

  (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 在 potassium carbonate 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 1-[2,2-dimethyl-(4S)-1,3-dioxolan-4-yl]-(1S)-heptan-1-ol
  参考文献：
  名称：

  Stereoselective total synthesis of microcarpalide

  摘要：

  A stereoselective total synthesis of microcarpalide using ring-closing metathesis (RCM) as a key step is reported. L-Ascorbic acid was used as a chiral pool material for the construction of the olefinic alcohol and an asymmetric aldol reaction provided the chiral precursor for the synthesis of olefinic acid. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.024

文献信息

• Stereoselective total synthesis of microcarpalide
  作者：G.V.M. Sharma、Govardhan R. Cherukupalli

  DOI：10.1016/j.tetasy.2006.03.024

  日期：2006.4

  A stereoselective total synthesis of microcarpalide using ring-closing metathesis (RCM) as a key step is reported. L-Ascorbic acid was used as a chiral pool material for the construction of the olefinic alcohol and an asymmetric aldol reaction provided the chiral precursor for the synthesis of olefinic acid. (c) 2006 Elsevier Ltd. All rights reserved.
• Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine
  作者：Geraldine C. B. Harriman、Anne F. Poirot、Elie Abushanab、Rose Marie Midgett、Johanna D. Stoeckler

  DOI：10.1021/jm00100a025

  日期：1992.10

  The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were Cl'- and nor-Cl'-(+)-EHNA derivatives. When tested with calf spleen ADA, Cl'-OH- and nor-Cl'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-Cl' derivatives.