(2S,3S)-2,3-epoxy-6-methylheptan-1-ol | 1247042-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,3S)-2,3-epoxy-6-methylheptan-1-ol
• 英文别名: [(2S,3S)-3-(3-methylbutyl)oxiran-2-yl]methanol
• CAS: 1247042-85-8
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: ORVOCSOGPCVFSP-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-epoxy-6-methylheptan-1-ol 在 sodium periodate 、 ruthenium(III) trichloride hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (2R,3S)-2,3-epoxy-6-methylheptanoic acid
  参考文献：
  名称：

  Concise synthesis of AHMHA unit in perthamide C. Structural and stereochemical revision of perthamide C

  摘要：

  Diastereomers of 3-amino-2-hydroxy-6-methylheptanoic acid (AHMHA), a new amino acid unit in perthamides C and D, have been synthesized from commercially available 4-methylpentanol in a concise manner and 50% average overall yield. Comparison of the H-1 and C-13 NMR data, optical rotation data and Marfey's analysis of the resulting isomers with the natural fragment unambiguously allowed the configurational assignment of the natural residue as (2R,3R). A structural revision of perthamides C and D is also reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.060
• 作为产物：
  描述：

  (E)-6-methylhept-2-en-1-ol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二乙酯 、 iron(II) sulfate 、 酒石酸 作用下， 以 癸烷 、 二氯甲烷 、 水 为溶剂， 反应 25.5h， 以90%的产率得到(2S,3S)-2,3-epoxy-6-methylheptan-1-ol
  参考文献：
  名称：

  Concise synthesis of AHMHA unit in perthamide C. Structural and stereochemical revision of perthamide C

  摘要：

  Diastereomers of 3-amino-2-hydroxy-6-methylheptanoic acid (AHMHA), a new amino acid unit in perthamides C and D, have been synthesized from commercially available 4-methylpentanol in a concise manner and 50% average overall yield. Comparison of the H-1 and C-13 NMR data, optical rotation data and Marfey's analysis of the resulting isomers with the natural fragment unambiguously allowed the configurational assignment of the natural residue as (2R,3R). A structural revision of perthamides C and D is also reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.060

文献信息

• Concise synthesis of AHMHA unit in perthamide C. Structural and stereochemical revision of perthamide C
  作者：Valentina Sepe、Maria Valeria D’Auria、Giuseppe Bifulco、Raffaella Ummarino、Angela Zampella

  DOI：10.1016/j.tet.2010.07.060

  日期：2010.9

  Diastereomers of 3-amino-2-hydroxy-6-methylheptanoic acid (AHMHA), a new amino acid unit in perthamides C and D, have been synthesized from commercially available 4-methylpentanol in a concise manner and 50% average overall yield. Comparison of the H-1 and C-13 NMR data, optical rotation data and Marfey's analysis of the resulting isomers with the natural fragment unambiguously allowed the configurational assignment of the natural residue as (2R,3R). A structural revision of perthamides C and D is also reported. (C) 2010 Elsevier Ltd. All rights reserved.