methyl (3R,4S)-3-hydroxy-4-methylhexanoate | 102230-99-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (3R,4S)-3-hydroxy-4-methylhexanoate
• CAS: 102230-99-9
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: IHQUHJQCUGFAPE-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-(-)-2-甲基-1-丁醇 在 lithium diisopropyl amide 作用下， 生成 methyl (3R,4S)-3-hydroxy-4-methylhexanoate
  参考文献：
  名称：

  阿维菌素b 1a螺缩醛单元的对映体合成

  摘要：

  阿维菌素B 1a的螺缩醛单元（C 15 -C 28）已通过利用立体控制的贝克酵母还原法进行对映体特异性合成。

  DOI：

  10.1016/s0040-4039(00)85191-6

文献信息

• The Scent of Bacteria: Headspace Analysis for the Discovery of Natural Products
  作者：Christian A. Citron、Patrick Rabe、Jeroen S. Dickschat

  DOI：10.1021/np300468h

  日期：2012.10.26

  Volatile compounds released by 50 bacterial strains, 45 of them actinobacteria in addition to three chloroflexi and two myxobacteria, have been collected by use of a closed-loop stripping apparatus, and the obtained headspace extracts have been analyzed by GC-MS. Excluding terpenes that have recently been published elsewhere, 254 compounds from all kinds of compound classes have been identified. For unambiguous compound identification several reference compounds have been synthesized. Among the detected volatiles 12 new natural products have been found, in addition to mellein, which was released by Saccharopolyspora erythraea. The iterative PKS for this compound has recently been identified by in vitro experiments, but mellein production in S. erythraea has never been reported before. These examples demonstrate that headspace analysis is an important tool for the discovery of natural products that may be overlooked using conventional techniques. The method is alos useful for feeding experiments with isotopically labeled precursors and was applied to investigate the biosynthesis of the unusual nitrogen compound 1-nitro-2-methylpropane, which arises from valine. Furthermore, several streptomycetes emitted compounds that were previously recognized as insect pheromones, thus questioning if bacterial symbionts are involved in insect communication.
• A Synthetic Approach to 3-Hydroxy 4-Substituted Carboxylic Acids based on the Stereoselective Reduction of 1-Trimethylsilyl-1-alkyn-3-ones
  作者：Carme Alemany、Jordi Bach、Jordi Garcia、Marta López、Ana B. Rodrı́guez

  DOI：10.1016/s0040-4020(00)00905-4

  日期：2000.11

  The oxazaborolidine-mediated reduction of chiral, 4-substituted 1-trimethylsilyl-1-alkyn-3-ones followed by hydroboration affords syn or anti 3-hydroxy 4-substituted carboxylic acids, common substructures of a number of biologically active macrolides, peptides and depsipeptides, with high control on the new C(3) stereocenter. This strategy has been applied to the synthesis of (3S,4S)-3-hydroxy-4-methylheptanoic acid and of N-Boc-statine, constituents of permentin A and pepstatin, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Enantiospecific synthesis of the spiroacetal unit of avermectin b1a
  作者：Masahiro Hirama、Takeshi Nakamine、Shô Itô

  DOI：10.1016/s0040-4039(00)85191-6

  日期：1986.1

  The spiroacetal unit (C15−C28) of avermectin B1a has been enantiospecifically synthesized by taking advantage of stereocontrolled baker's yeast reduction.

  阿维菌素B 1a的螺缩醛单元（C 15 -C 28）已通过利用立体控制的贝克酵母还原法进行对映体特异性合成。