(E,4R,5R)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate | 848566-32-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E,4R,5R)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate
• CAS: 848566-32-5
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: GRXHNZOXJNIXKZ-SJXIGLKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  20.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E,4R,5R)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate 在 吡啶 、 4-二甲氨基吡啶 、 AD-mix-α 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 9.0h， 生成 (3R,4S,5S)-5-(2'-benzyloxy-(1'R)-1'-acetoxy-ethyl)-3,4-diacetoxy-dihydro-furan-2(3H)-one
  参考文献：
  名称：

  De Novo Enantioselective Syntheses of Galacto-Sugars and Deoxy Sugars via the Iterative Dihydroxylation of Dienoate

  摘要：

  [GRAPHICS]An efficient route to various sugar lactones has been developed. Key to the overall transformation is the sequential osmium-catalyzed dihydroxylation of 2,4-dienoates. The simplest (one-step/racemic) example of this reaction occurs when the dihydroxylation is performed with aqueous NMO in MeOH. When the first dihydroxylation is performed using the AD-mix procedure, an enantioselective variant results. When a matched AD-mix procedure is used for the second dihydroxylation, an exceedingly diastereo- and enantioselective synthesis of galacto-1,4-lactone results.

  DOI：

  10.1021/ol050044i
• 作为产物：
  描述：

  (2E,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate 在 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 以90%的产率得到(E,4R,5R)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate
  参考文献：
  名称：

  De Novo Enantioselective Syntheses of Galacto-Sugars and Deoxy Sugars via the Iterative Dihydroxylation of Dienoate

  摘要：

  [GRAPHICS]An efficient route to various sugar lactones has been developed. Key to the overall transformation is the sequential osmium-catalyzed dihydroxylation of 2,4-dienoates. The simplest (one-step/racemic) example of this reaction occurs when the dihydroxylation is performed with aqueous NMO in MeOH. When the first dihydroxylation is performed using the AD-mix procedure, an enantioselective variant results. When a matched AD-mix procedure is used for the second dihydroxylation, an exceedingly diastereo- and enantioselective synthesis of galacto-1,4-lactone results.

  DOI：

  10.1021/ol050044i

文献信息

• 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。
• 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.