ethyl (4R)-benzyloxy-5-hydroxy-trans-2-pentenoate | 119770-84-2

• 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: ethyl (4R)-benzyloxy-5-hydroxy-trans-2-pentenoate
• 英文别名: ethyl (-)-[R-(E)]-4-O-benzyl-4,5-dihydroxy-2-pentenoate；ethyl (E,4R)-5-hydroxy-4-phenylmethoxypent-2-enoate
• CAS: 119770-84-2
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: DZLMRJMJSONCAL-MMQHEFTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2R,3R)-(-)-2-苄氧基-1,3,4-丁三醇 在 sodium periodate 、 sodium hydride 作用下， 以 水 为溶剂， 生成 ethyl (4R)-benzyloxy-5-hydroxy-trans-2-pentenoate
  参考文献：
  名称：

  Jaeger, Volker; Wehner, Volkmar, Angewandte Chemie, 1989, vol. 101, # 4, p. 512 - 513

  摘要：

  DOI：

文献信息

• (−)-2-O-BENZYL-L-GLYCERALDEHYDE AND ETHYL (R,E)-4-O-BENZYL-4,5-DIHYDROXY-2-PENTENOATE
  作者：Steuer、Wehner、Lieberknecht、Jäger

  DOI：10.15227/orgsyn.074.0001

  日期：——
• Selective conjugate addition of nitromethane to enoates derived from d-mannitol and l-tartaric acid
  作者：Américo C. Pinto、Cleide B.L. Freitas、Ayres G. Dias、Vera L.P. Pereira、Bernard Tinant、Jean-Paul Declercq、Paulo R.R. Costa

  DOI：10.1016/s0957-4166(02)00230-6

  日期：2002.6

  The conjugate addition of nitromethane to enoates prepared from D-(+)-mannitol, substituted at the alpha-position by a methyl or a benzyl group, was investigated. While excellent syn-selectivity (d.e. >90%) was obtained from a-benzyl enoates (used as a mixture of epimers, E/Z=1.8:1), for alpha-methyl enoates the selectivity depended on the stereochemistry of the double bond in the acceptor (d.e. >90% for the (Z)-enoate and 50% for the (E)-enoate). In all cases, a mixture of epimers was formed at the newly generated stereocenter at the a-position. The epimeric syn-adducts were transformed into the corresponding pure alpha,beta,gamma-trisubstituted gamma-butyrolactones by cyclization in acid medium followed by epimerization of the stereocenter at the a-position in DBU/CH2Cl2. When enoates derived from L-tartaric acid were used as acceptors, syn-selective conjugate additions were also observed (d.e. >90% for the (Z)-isomer and 50% for the (E)-isomer). The configuration at the newly generated stereogenic centers were assigned based on X-ray analyses, H-1-H-1 coupling constants and NOE experiments in NMR spectroscopy. (C) 2002 Elsevier Science Ltd. All rights reserved.
• JAGER, VOLKER;WEHNER, VOLKMAR, ANGEW. CHEM., 101,(1989) N, C. 512-513
  作者：JAGER, VOLKER、WEHNER, VOLKMAR

  DOI：——

  日期：——
• Jaeger, Volker; Wehner, Volkmar, Angewandte Chemie, 1989, vol. 101, # 4, p. 512 - 513
  作者：Jaeger, Volker、Wehner, Volkmar

  DOI：——

  日期：——