(2S,3S,4R,5S)-ethyl 4-(4-methoxyphenoxy)-2,3,5-trihydroxyheptanoate | 852611-13-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S)-ethyl 4-(4-methoxyphenoxy)-2,3,5-trihydroxyheptanoate
• 英文别名: ethyl (2S,3S,4R,5S)-2,3,5-trihydroxy-4-(4-methoxyphenoxy)heptanoate
• CAS: 852611-13-3
• 化学式: C₁₆H₂₄O₇
• 分子量: 328.362
• InChiKey: FCRBTGVVAFRGLT-ZQDZILKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S)-ethyl 4-(4-methoxyphenoxy)-2,3,5-trihydroxyheptanoate 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 5.0h， 以86%的产率得到(3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-ethyl-tetrahydro-3,4-dihydroxypyran-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：

  (E)-ethyl 3-((4S,5S)-5-ethyl-2-oxo-1,3-dioxolan-4-yl)acrylate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 三苯基膦 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 (2S,3S,4R,5S)-ethyl 4-(4-methoxyphenoxy)-2,3,5-trihydroxyheptanoate
  参考文献：
  名称：

  De novo synthesis of galacto-sugar δ-lactones via a catalytic osmium/palladium/osmium reaction sequence

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2005.03.029

文献信息

• 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.
• De novo asymmetric syntheses of C-4-substituted sugars via an iterative dihydroxylation strategy
  作者：Md. Moinuddin Ahmed、George A. O’Doherty

  DOI：10.1016/j.carres.2006.03.024

  日期：2006.7

  highly efficient route to various C-4 substituted sugar lactones has been developed. The key to the overall transformation is the sequential osmium-catalyzed dihydroxylation reaction of substituted 2,4-dienoates and an allylic substitution at the C-4 position. When the Sharpless AD-mix procedure is used in a matched sense for the second dihydroxylation reaction, it results in an exceedingly diastereo-

  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。