diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-hydroxy-octanedioate | 444340-68-5

• 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: diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-hydroxy-octanedioate
• 英文别名: diethyl (4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-hydroxyoctanedioate
• CAS: 444340-68-5
• 化学式: C₁₈H₃₆O₆Si
• 分子量: 376.566
• InChiKey: FVSUGIDXOLIKAZ-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-hydroxy-octanedioate 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~80.0 ℃ 、344.74 kPa 条件下， 反应 10.5h， 生成 (5R,6S)-5-(tert-butyldimethylsilanyloxy)-6-(2-ethoxycarbonylethyl)-piperidin-2-one
  参考文献：
  名称：

  An expedient stereoselective synthesis of polysubstituted piperidin-2-ones

  摘要：

  A versatile approach to the synthesis of various chiral substituted azido compounds is described. The utility and flexibility of this methodology has been demonstrated by the stereoselective synthesis of optically active polysubstituted piperidin-2-ones which are promising precursors for the synthesis of several indolizidine and piperidine alkaloids. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00015-7
• 作为产物：
  描述：

  (2E,6E)-(4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-octa-2,6-dienedioic acid diethyl ester 在 palladium on activated charcoal 氢气 作用下， 反应 0.5h， 以87%的产率得到diethyl (4R,5R)-4-(tert-butyldimethylsilanyloxy)-5-hydroxy-octanedioate
  参考文献：
  名称：

  An expedient stereoselective synthesis of polysubstituted piperidin-2-ones

  摘要：

  A versatile approach to the synthesis of various chiral substituted azido compounds is described. The utility and flexibility of this methodology has been demonstrated by the stereoselective synthesis of optically active polysubstituted piperidin-2-ones which are promising precursors for the synthesis of several indolizidine and piperidine alkaloids. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)00015-7

文献信息

• Synthesis of γ-lactones by desymmetrization. A synthesis of (−)-muricatacin
  作者：M. Teresa Barros、M. Adilia Januario Charmier、Christopher D. Maycock、Thierry Michaud

  DOI：10.1016/j.tet.2008.10.020

  日期：2009.1

  A short synthesis of the natural potent cytotoxic agent (-)-muricatacin 1 and related unsaturated lactones from a versatile common intermediate, dienedioate 2, derived from D-mannitol or tartaric acid, is described. The strategy depends upon the desymmetrization of 7 by dihydroxylation and elaboration of the hydroxy alkyl sidechain. A route to unsaturated lactones is also described using a cis selective Wittig reaction. Since the enantiomers of 2 are available from the corresponding tartaric acids, this method provides access to both enantiomers of the described compounds and a wide range of derivatives. (C) 2008 Elsevier Ltd. All rights reserved.