(2S,3R)-3-bromo-2-hydroxy-6-methylheptanoate | 1247042-87-0

• 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: (2S,3R)-3-bromo-2-hydroxy-6-methylheptanoate
• 英文别名: methyl (2S,3R)-3-bromo-2-hydroxy-6-methylheptanoate
• CAS: 1247042-87-0
• 化学式: C₉H₁₇BrO₃
• 分子量: 253.136
• InChiKey: WQJKURMZAFRATM-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-bromo-2-hydroxy-6-methylheptanoate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以92%的产率得到(2R,3S)-3-azido-2-hydroxy-6-methylheptanoate
  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：

  (2R,3S)-methyl 2,3-epoxy-6-methylheptanoate 在 magnesium bromide ethyl etherate 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以98%的产率得到(2S,3R)-3-bromo-2-hydroxy-6-methylheptanoate
  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.