(3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
• 英文别名: (4R,5S,6S)-4-hydroxy-6-[(4S)-4-hydroxyhexyl]-5-methyloxan-2-one
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: AHSYORCLENEWMX-MMWGEVLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 2-[(4R,5R,6S)-5-methyl-2-phenyl-6-[(4S)-4-phenylmethoxyhex-2-ynyl]-1,3-dioxan-4-yl]acetate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 以85%的产率得到(3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
  参考文献：
  名称：

  Stereoselective synthesis of (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone

  摘要：

  A stereoselective synthesis of the pentaketide lactone (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid delta-lactone has been achieved. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2006.11.171

文献信息

• Synthesis of (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
  作者：Tushar K. Chakraborty、Rajib K. Goswami

  DOI：10.1016/j.tetlet.2004.08.099

  日期：2004.10

  Radical-mediated opening of a chiral trisubstituted epoxy alcohol using cp(2)TiCl furnished the '2-methyl-1,3-diol' moiety with the desired stereochemistry, which led to a total synthesis of (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid delta-lactone 1. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
  作者：Gowravaram Sabitha、Peddabuddi Gopal、Jhillu S. Yadav

  DOI：10.1016/j.tetasy.2009.06.008

  日期：2009.7

  The total synthesis of lactone I has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions. (C) 2009 Published by Elsevier Ltd.
• Stereoselective synthesis of (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
  作者：J.S. Yadav、P. Murali Krishna Reddy、P. Venkatram Reddy

  DOI：10.1016/j.tetlet.2006.11.171

  日期：2007.2

  A stereoselective synthesis of the pentaketide lactone (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid delta-lactone has been achieved. (c) 2006 Published by Elsevier Ltd.