ethyl (2E,4R,5R)-4,5-dihydroxy-4-methylhex-2-enoate | 342900-76-9

• 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: ethyl (2E,4R,5R)-4,5-dihydroxy-4-methylhex-2-enoate
• 英文别名: (E,4R,5R)-ethyl 4,5-dihydroxy-4-methylhex-2-enoate；ethyl (E,4R,5R)-4,5-dihydroxy-4-methylhex-2-enoate
• CAS: 342900-76-9
• 化学式: C₉H₁₆O₄
• 分子量: 188.224
• InChiKey: UJZVDYPDEOSQDQ-VZRAIFRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2E,4R,5R)-4,5-dihydroxy-4-methylhex-2-enoate 在 tris-(dibenzylideneacetone)dipalladium(0) 吡啶 、 甲酸 、 三丁基膦 、 potassium tert-butylate 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 55.33h， 生成 ethyl 2-[(4S,5R,6R)-5,6-dimethyl-2-phenyl-1,3-dioxan-4-yl]acetate
  参考文献：
  名称：

  Asymmetric Synthesis of the C(33) - C(37) Fragment of Amphotericin B

  摘要：

  We have devised an expeditious. efficient, asymmetric synthesis of the C(33)-C(37) fragment of amphotericin B that proceeds in 14 steps and 16% overall yield from tiglic aldehyde ((E)-2-methylbut-2-enal) with complete stereocontrol. The route described herein relies on the application of recently developed methods in catalytic asymmetric synthesis for stereocontrol through enantio- and diastereoselective functionalization of a substituted sorbate derivative.

  DOI：

  10.1002/1522-2675(20010321)84:3<613::aid-hlca613>3.0.co;2-4
• 作为产物：
  描述：

  反式-2-甲基-2-丁烯醛 在 甲基磺酰胺 、 potassium carbonate 四氧化锇 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 生成 ethyl (2E,4R,5R)-4,5-dihydroxy-4-methylhex-2-enoate
  参考文献：
  名称：

  De Novo Synthesis of 2-Substituted syn-1,3-Diols via an Iterative Asymmetric Hydration Strategy

  摘要：

  The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).

  DOI：

  10.1021/jo061200h

文献信息

• Asymmetric Synthesis of the C(33) - C(37) Fragment of Amphotericin B
  作者：Joakim Tholander、Erick M. Carreira

  DOI：10.1002/1522-2675(20010321)84:3<613::aid-hlca613>3.0.co;2-4

  日期：2001.3.21

  We have devised an expeditious. efficient, asymmetric synthesis of the C(33)-C(37) fragment of amphotericin B that proceeds in 14 steps and 16% overall yield from tiglic aldehyde ((E)-2-methylbut-2-enal) with complete stereocontrol. The route described herein relies on the application of recently developed methods in catalytic asymmetric synthesis for stereocontrol through enantio- and diastereoselective functionalization of a substituted sorbate derivative.
• De Novo Synthesis of 2-Substituted <i>syn</i>-1,3-Diols via an Iterative Asymmetric Hydration Strategy
  作者：Md. Moinuddin Ahmed、Matthew S. Mortensen、George A. O'Doherty

  DOI：10.1021/jo061200h

  日期：2006.9.1

  The enantioselective syntheses of several protected 4-substituted syn-3,5-dihydroxy carboxylic esters have been achieved from the corresponding achiral (E,E)- or (E,Z)-1,3-dienoates. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form gamma-substituted delta-hydroxy-1-enoates. The resulting delta-hydroxy-1-enoates are subsequently converted into benzylidene-protected 4-substituted syn-3,5-dihydroxy carboxylic esters in one step. The benzylidene-protected 3,5-dihydroxy carboxylic esters are produced in good overall yields (20-54%) and high enantiomeric excess (73- 97% ee).