(4S,5R)-1,3-dibenzyl-5-[(2E)-3-phenyl-2-propenyloxycarbonyl]-2-oxo-imidazolidine-4-carboxylic acid | 1055329-68-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R)-1,3-dibenzyl-5-[(2E)-3-phenyl-2-propenyloxycarbonyl]-2-oxo-imidazolidine-4-carboxylic acid
• 英文别名: (4S,5R)-1,3-dibenzyl-2-oxo-5-[(3-phenylallyloxy)carbonyl]imidazolidine-4-carboxylic acid；(4S,5R)-1,3-dibenzyl-2-oxo-5-[(E)-3-phenylprop-2-enoxy]carbonylimidazolidine-4-carboxylic acid
• CAS: 1055329-68-4
• 化学式: C₂₈H₂₆N₂O₅
• 分子量: 470.525
• InChiKey: WZZCEESSPITQMI-QBQLRLMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1,3-dibenzyl-5-[(2E)-3-phenyl-2-propenyloxycarbonyl]-2-oxo-imidazolidine-4-carboxylic acid 在 钾硼氢 、 calcium chloride 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以98%的产率得到(3aS,6aR)-1,3-二苄基四氢-1H-呋喃并[3,4-d]咪唑-2,4-二酮
  参考文献：
  名称：

  An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide

  摘要：

  The highly enantioselective total synthesis of (+)-biotin 1 via the Hoffmann-Roche lactone-thiolactone strategy has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 with an overall yield of 35%. Two contiguous stereogenic centers at C-3a and C-6a were established through a rapid cinchona alkaloid-based sulfonamide-mediated enantioselective alcoholysis of meso-cyclic anhydride 3 to afford (4S,5R)-cinnamyl hemiester 4h, the direct precursor to (3aS,6aR)-lactone 5 with high enantioselectivity. A one-pot installation of the 4-carboxybutyl side chain was accomplished by a Fukuyama coupling reaction of (3aS,6aR)-thiolactone 6 with the organozinc reagent prepared from ethyl 5-bromopentanoate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.041
• 作为产物：
  描述：

  (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 、 3-苯基丙-2-烯-1-醇 在 O-propargylquinine 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以81.3%的产率得到(4S,5R)-1,3-dibenzyl-5-[(2E)-3-phenyl-2-propenyloxycarbonyl]-2-oxo-imidazolidine-4-carboxylic acid
  参考文献：
  名称：

  （+）-生物素的合成研究，第11部分：金鸡纳生物碱介导的内消旋环酸酐的不对称醇解在（+）-生物素的全合成中的应用

  摘要：

  从顺式-1,3-二苄基-2-氧代咪唑烷-4,5-二羧酸（2）开始，已经完成了一种实用的不对称全合成（+）-生物素的方法（1）。这种方法提供的一个高度对映选择性的醇解的内消旋-环酐3代入式（4小号，5 - [R）-cinnamyl半酯4介导的金鸡纳生物碱。该合成的另一个吸引人的特征涉及在（3 aS，6 aR）-硫代内酯7中C-4处4-羧基丁基链的可回收钯纳米粒子催化的组装 采用改进的福山型交叉偶联反应

  DOI：

  10.1002/adsc.200800151

文献信息

• Total synthesis of (+)-biotin via a quinine-mediated asymmetric alcoholysis of meso-cyclic anhydride strategy
  作者：Jian Huang、Fei Xiong、Fen-Er Chen

  DOI：10.1016/j.tetasy.2008.05.020

  日期：2008.6

  A concise asymmetric total synthesis of (+)-biotin 1 has been accomplished in which the absolute stereochemistry of C-3a, C-6a of 1 was established by utilizing an efficient and practical quinine-mediated asymmetric alcoholysis of meso-cyclic anhydride 2 in a single step, the C-4 stereochemistry was installed by a direct stereoselective ionic hydrogenation of the thiolactol 7. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthetic Studies on (+)‐Biotin, Part 11: Application of<i>Cinchona</i>Alkaloid‐Mediated Asymmetric Alcoholysis of<i>meso</i>‐Cyclic Anhydride in the Total Synthesis of (+)‐Biotin
  作者：Hui‐Fang Dai、Wen‐Xue Chen、Lei Zhao、Fei Xiong、Hao Sheng、Fen‐Er Chen

  DOI：10.1002/adsc.200800151

  日期：2008.7.7

  practical and asymmetric process for the total synthesis of (+)-biotin (1) has been accomplished starting from cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid (2). This approach features a highly enantioselective alcoholysis of meso-cyclic anhydride 3 into (4S,5R)-cinnamyl hemiester 4 mediated by Cinchona alkaloids. Another attractive feature of this synthesis involves the use of recyclable palladium

  从顺式-1,3-二苄基-2-氧代咪唑烷-4,5-二羧酸（2）开始，已经完成了一种实用的不对称全合成（+）-生物素的方法（1）。这种方法提供的一个高度对映选择性的醇解的内消旋-环酐3代入式（4小号，5 - [R）-cinnamyl半酯4介导的金鸡纳生物碱。该合成的另一个吸引人的特征涉及在（3 aS，6 aR）-硫代内酯7中C-4处4-羧基丁基链的可回收钯纳米粒子催化的组装 采用改进的福山型交叉偶联反应
• An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide
  作者：Fei Xiong、Xu-Xiang Chen、Fen-Er Chen

  DOI：10.1016/j.tetasy.2010.03.041

  日期：2010.4

  The highly enantioselective total synthesis of (+)-biotin 1 via the Hoffmann-Roche lactone-thiolactone strategy has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 with an overall yield of 35%. Two contiguous stereogenic centers at C-3a and C-6a were established through a rapid cinchona alkaloid-based sulfonamide-mediated enantioselective alcoholysis of meso-cyclic anhydride 3 to afford (4S,5R)-cinnamyl hemiester 4h, the direct precursor to (3aS,6aR)-lactone 5 with high enantioselectivity. A one-pot installation of the 4-carboxybutyl side chain was accomplished by a Fukuyama coupling reaction of (3aS,6aR)-thiolactone 6 with the organozinc reagent prepared from ethyl 5-bromopentanoate. (C) 2010 Elsevier Ltd. All rights reserved.