(4S,5R)-1,3-dibenzyl-5-(propargyloxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid | 1055329-67-3

• 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-(propargyloxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
• 英文别名: (4S,5R)-1,3-dibenzyl-2-oxo-5-prop-2-ynoxycarbonylimidazolidine-4-carboxylic acid
• CAS: 1055329-67-3
• 化学式: C₂₂H₂₀N₂O₅
• 分子量: 392.411
• InChiKey: KGPYNZIVBJTQNU-RBUKOAKNSA-N

物化性质

• 熔点：
  135.8-137.8 °C(Solv: ethyl acetate (141-78-6); cyclohexane (110-82-7))
• 沸点：
  624.3±55.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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-(propargyloxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid 在 sodium tetrahydroborate 、 calcium chloride 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 (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：

  一种新的具有成本效益的双功能硫脲为有机小分子的高对映选择性醇解观-环状酸酐：增强的对映选择性的配置反转

  摘要：

  Abstractmagnified imageA novel inexpensive thiourea bifunctional organocatalyst which can promote the highly enantioselective (up to 95% ee) alcoholysis of meso‐cyclic anhydrides has been developed. Computational studies on the catalytic process as well as a synthetic application of this new catalyst are also presented.

  DOI：

  10.1002/adsc.200800761
• 作为产物：
  描述：

  (4S,5R)-1,3-dibenzyl-1H-furo[3,4-d]imidazole-2,4,6-trione 、 2-丙炔-1-醇 在 C₂₂H₂₈N₄OS 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.17h， 以95%的产率得到(4S,5R)-1,3-dibenzyl-5-(propargyloxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
  参考文献：
  名称：

  [EN] A PREPARATION METHOD OF (4S,5R)-SEMIESTER
  [FR] PROCÉDÉ DE PRÉPARATION DE (4S,5R)-SEMI-ESTER

  摘要：

  一种制备(4S,5R)-半酯的方法，其中环酸酐在9-epiquininurea存在下与醇进行对映选择性环开反应。利用这种方法，可以在室温下高产率高立体选择性地制备(4S,5R)-半酯。

  公开号：

  WO2009146607A1

文献信息

• 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.
• 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.
• A Novel Cost-Effective Thiourea Bifunctional Organocatalyst for Highly Enantioselective Alcoholysis of<i>meso</i>-Cyclic Anhydrides: Enhanced Enantioselectivity by Configuration Inversion
  作者：Su-Xi Wang、Fen-Er Chen

  DOI：10.1002/adsc.200800761

  日期：2009.3

  Abstractmagnified imageA novel inexpensive thiourea bifunctional organocatalyst which can promote the highly enantioselective (up to 95% ee) alcoholysis of meso‐cyclic anhydrides has been developed. Computational studies on the catalytic process as well as a synthetic application of this new catalyst are also presented.
• [EN] A PREPARATION METHOD OF (4S,5R)-SEMIESTER<br/>[FR] PROCÉDÉ DE PRÉPARATION DE (4S,5R)-SEMI-ESTER
  申请人：DSM IP ASSETS BV

  公开号：WO2009146607A1

  公开（公告）日：2009-12-10

  A preparation method of (4S,5R)-semiester in which cycloanhydride conducts enantioselective ring-opening with alcohol in the presence of 9-epiquininurea. With this method, (4S,5R)-semiester is prepared at room temperature with high yield and high stereoselectivity.

  一种制备(4S,5R)-半酯的方法，其中环酸酐在9-epiquininurea存在下与醇进行对映选择性环开反应。利用这种方法，可以在室温下高产率高立体选择性地制备(4S,5R)-半酯。