(E,4R,5R)-ethyl 4-(4-methoxyphenoxy)-5-hydroxy-hex-2-enoate | 852611-17-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E,4R,5R)-ethyl 4-(4-methoxyphenoxy)-5-hydroxy-hex-2-enoate
• 英文别名: ethyl (2E,4R,5R)-5-hydroxy-4-(4-methoxyphenoxy)hex-2-enoate；ethyl (E,4R,5R)-5-hydroxy-4-(4-methoxyphenoxy)hex-2-enoate
• CAS: 852611-17-7
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: DHUWWQHIWRBPFY-YCNBAEJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E,4R,5R)-ethyl 4-(4-methoxyphenoxy)-5-hydroxy-hex-2-enoate 在 AD-mix-β 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 水 、 叔丁醇 、 苯 为溶剂， 反应 5.0h， 生成 (3S,4S,5S,6S)-5-(4-methoxyphenoxy)-tetrahydro-3,4-dihydroxy-6-methylpyran-2-one
  参考文献：
  名称：

  通过迭代二羟基化策略从头开始不对称合成C-4-取代的糖。

  摘要：

  已经开发了一种短且高效的途径来制备各种C-4取代的糖内酯。总体转化的关键是取代的2，4-二烯酸酯的催化的二羟基化反应和C-4位置的烯丙基取代。当将Sharpless AD-mix程序以匹配的方式用于第二个二羟基化反应时，会导致几种C-4取代糖的非对映和对映选择性合成。

  DOI：

  10.1016/j.carres.2006.03.024
• 作为产物：
  描述：

  4-甲氧基苯酚 、 (4R,5R)-3-(5-Methyl-2-oxo-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(E,4R,5R)-ethyl 4-(4-methoxyphenoxy)-5-hydroxy-hex-2-enoate
  参考文献：
  名称：

  A formal, stereoselective synthesis of the natural tetrahydropyran derivative ophiocerin D

  摘要：

  A short, formal stereoselective synthesis of the naturally occurring tetrahydropyran derivative ophiocerin D is reported. The four stereocenters of the molecule were created with the aid of two Sharpless asymmetric dihydroxylations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.013

文献信息

• Intramolecular conjugate addition of γ- and δ-trichloroacetimidoyloxy-α,β-unsaturated esters in an acyclic system
  作者：Yoshitaka Matsushima、Jun Kino

  DOI：10.1016/j.tet.2008.02.061

  日期：2008.4

  An intramolecular conjugate addition of γ- and δ-trichloroacetimidoyloxy-α,β-unsaturated esters, a new way to construct 1,2-amino or 1,3-amino alcohol moieties in an acyclic system, is described. Very concise synthesis of d-vancosamine and 3-epi-d-vancosamine derivatives was also achieved utilizing this methodology.

  描述了γ-和δ-三氯乙二酰亚胺基氧基-α，β-不饱和酯的分子内共轭加成，这是在无环体系中构建1,2-氨基或1,3-氨基醇部分的新方法。使用该方法还可以实现非常简明的d-vancosamine和3- epi - d- d-vancosamine衍生物的合成。
• Synthesis of<i>N</i>-Bz-Protected D-Daunosamine and D-Ristosamine by Silica Gel Promoted Intramolecular Conjugate Addition of Trichloroacetimidates obtained from Osmundalactone and Its Epimer
  作者：Yoshitaka Matsushima、Jun Kino

  DOI：10.1002/ejoc.200901402

  日期：2010.4

  osmundalactone and its epimer unexpectedly undergo intramolecular conjugate addition during silica gel chromatography to produce oxazolines in excellent yields. The novel, simple synthesis of N-Bz-protected D-daunosamine and D-ristosamine from these oxazolines is described in this paper.

  由桂皮内酯及其差向异构体制备的三氯乙酰亚胺在硅胶色谱过程中出人意料地进行了分子内共轭加成，以优异的产率生产恶唑啉。本文描述了从这些恶唑啉中新颖、简单地合成 N-Bz 保护的 D-道诺胺和 D-利索胺。
• De novo synthesis of galacto-sugar δ-lactones via a catalytic osmium/palladium/osmium reaction sequence
  作者：Md. Moinuddin Ahmed、George A. O’Doherty

  DOI：10.1016/j.tetlet.2005.03.029

  日期：2005.4

  A highly efficient route to various 1,5-galacto-sugar lactones from dienoates has been developed by using three catalytic reactions. These reactions include (i) an enantioselective osmium-catalyzed dihydroxylation, (ii) a regio- and diastereoselective palladium-catalyzed pi-allyl alkylation with p-methoxyphenol for alcohol differentiation and protection, and (iii) a diastereoselective dihydroxylation that can be improved using matched emantioselective osmium-catalyzed dihydroxylation condition. (c) 2005 Elsevier Ltd. All rights reserved.