(4S,5S,E)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylhept-2-enoate | 914366-93-1

• 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: (4S,5S,E)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylhept-2-enoate
• 英文别名: (E,4S,5S)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylhept-2-enoate；ethyl (E,4S,5S)-5-hydroxy-4-methyl-7-phenylmethoxyhept-2-enoate
• CAS: 914366-93-1
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: NIRFFOHZKBDHGP-OOCSTFOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S,E)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylhept-2-enoate 在 甲醇 、 二异丁基氢化铝 、 magnesium 作用下， 以 二氯甲烷 为溶剂， 反应 5.25h， 生成 (5S,6S)-6-(2-(benzyloxy)ethyl)-5-methyltetrahydro-2H-pyran-2-ol
  参考文献：
  名称：

  Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

  摘要：

  A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1-C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.08.085
• 作为产物：
  描述：

  (E,4S,5S)-ethyl 7-benzyloxy-4,5-dihydroxy-4-methylhept-2-enoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 吡啶 、 甲酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.66h， 生成 (4S,5S,E)-ethyl 7-(benzyloxy)-5-hydroxy-4-methylhept-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

• Stereoselective Total Synthesis of Bistramide A
  作者：J. S. Yadav、Lakshindra Chetia

  DOI：10.1021/ol702095n

  日期：2007.10.1

  A highly stereoselective and convergent total synthesis of bistramide A is described. The salient feature of this synthesis is the construction of the spiroketal subunit by hydrolysis of dialkylated tosylmethyl isocyanide derivative derived via alkylation of TosMIC with suitably substituted halohydrin derivatives.

  描述了双立体酰胺A的高度立体选择性和收敛的全合成。该合成的显着特征是通过将TosMIC与合适取代的卤代醇衍生物进行烷基化而衍生的二烷基化的甲苯磺酰基甲基异氰化物衍生物的水解来构建螺环亚基。
• Synthetic studies on cytotoxic macrolides cruentarens A and B: stereoselective synthesis of the C8–C19 segment of cruentarens A and B
  作者：Busam Ramalinga Vara Prasad、Harshadas Mitaram Meshram

  DOI：10.1016/j.tetasy.2010.04.068

  日期：2010.8

  A stereoselective synthesis of the C8–C19 segment of cruentarens A and B, cytotoxic natural products, has been accomplished. The key steps involve a stereoselective radical cyclization, stereospecific methylation of a γ, δ-epoxy acrylate, nucleophilic epoxide ring opening and a cis-Wittig olefination.

  已经完成了对角质素A和B（细胞毒性天然产物）的C 8 –C 19片段的立体选择性合成。关键步骤包括立体选择性自由基环化，γ，δ-环氧丙烯酸酯的立体有择甲基化，亲核性环氧化物开环和顺式-Wittig烯化。