ethyl (3R,4R,5R)-5-O-benzoyl-shikimate | 1149345-81-2

• 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 (3R,4R,5R)-5-O-benzoyl-shikimate
• 英文别名: [(1R,5R,6R)-3-ethoxycarbonyl-5,6-dihydroxycyclohex-3-en-1-yl] benzoate
• CAS: 1149345-81-2
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: DBCUXCVVPPWZHO-MGPQQGTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (3R,4R,5R)-5-O-benzoyl-shikimate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以96%的产率得到ethyl (3R,4R,5R)-5-O-benzoyl-3,4-O-bis(methanesulfonyl)shikimate
  参考文献：
  名称：

  Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH

  摘要：

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.028
• 作为产物：
  描述：

  ethyl (3R,4S,5R)-5-O-benzoyl-3,4-O-isopropylideneshikimate 在 盐酸 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 6.0h， 以94%的产率得到ethyl (3R,4R,5R)-5-O-benzoyl-shikimate
  参考文献：
  名称：

  A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid

  摘要：

  Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by ail N-3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-0-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1 S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.027

文献信息

• Inversion of secondary chiral alcohols in toluene with the tunable complex of R3NR′COOH
  作者：Xiao-Xin Shi、Chun-Li Shen、Jian-Zhong Yao、Liang-Deng Nie、Na Quan

  DOI：10.1016/j.tetasy.2009.12.028

  日期：2010.3

  The S(N)2 reaction of enantiomerically pure sulfonates with the tunable complex of R3N-R'COOH in toluene has been extensively studied. It was revealed that the molar ratio of the tertiary amines and carboxylic acids in the complex of R3NR'COOH is crucial for the S(N)2 reaction, and should be tuned for each sulfonate to give the best yield. Fifteen sulfonates 1 and 3-13 (Scheme 2) were prepared and transformed into 22 corresponding inverted esters 2 and 14-24 (Scheme 2) in good to high yields. (C) 2010 Elsevier Ltd. All rights reserved.
• A novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (−)-shikimic acid
  作者：Liang-Deng Nie、Xiao-Xin Shi

  DOI：10.1016/j.tetasy.2008.11.027

  日期：2009.1

  Oseltamivir phosphate 1 was synthesized starting from a readily available acetonide, that is, ethyl (3R,4S,5R)-3,4-O-isopropylidene shikimate 2, through a new route via 11 steps and in 44% overall yield. The synthesis described in this article is characterized by two particular steps: the highly regioselective and stereoselective facile nucleophilic replacement of an OMs by ail N-3 group at the C-3 position of ethyl (3R,4S,5R)-3,4-O-bismethanesulfonyl-5-0-benzoyl shikimate 5, and the mild ring-opening of an aziridine with 3-pentanol at the C-1 position of ethyl (1 S,5R,6S)-7-acetyl-5-benzoyloxy-7-azabicyclo[4,1,0]hept-2-ene-3-carboxylate 8. (C) 2008 Elsevier Ltd. All rights reserved.