(4R,5S)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid | 87637-50-1

• 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: (4R,5S)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
• 英文别名: 1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxoimidazolidine-4-carboxylic acid；(4R,5S)-1,3-dibenzyl-2-oxo-5-propoxycarbonylimidazolidine-4-carboxylic acid
• CAS: 87637-50-1
• 化学式: C₂₂H₂₄N₂O₅
• 分子量: 396.443
• InChiKey: NFQQKLXLAFETNH-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S)-2-amino-1,1-diphenylpropan-1-ol;(4R,5S)-1,3-dibenzyl-2-oxo-5-propoxycarbonylimidazolidine-4-carboxylic acid 、 (S)-2-氨基-1,1-二苯基-1-丙醇 生成 (4R,5S)-1,3-dibenzyl-5-(n-propoxycarbonyl)-2-oxo-imidazolidine-4-carboxylic acid
  参考文献：
  名称：

  OHASHI, NAOHITO;SHIMAGO, KOZO;IKEDA, TAKAHARU;ISHIZUMI, KIKUO

  摘要：

  DOI：

文献信息

• Preparation of optically active cis-1,3-dibenzyl-hexahydro-1H-furo(3,4-d)imidazole-2,4-dione and its intermediates
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0084892A2

  公开（公告）日：1983-08-03

  A process for preparing an optically active cis-1,3-diben- zylhexahydro-1 H-furo[3,4-d]imidazole-2,4-dione of the formula: wherein an asterisk (*) indicates an asymmetric carbon, Bzl represents a benzyl group and the 3a- und 6a-positions take the cis-configuration, which comprises reducing selectively an optically acitve cis-imidazolidinedicarboxylic acid monoester of the formula: wherein R is a C1-C6 alkyl group and Bzl is as defined above with a reducing agent at either one of the carboxyl group and the alkoxycarbonyl group in the said monoester, followed by cyclization, the said monoester being that obtainable by hydrolysis of a cis-imidazolidinedicarboxylic acid diester of the formula: wherein R and Bzl are each as defined above with an enzymatic material capable of hydrolyzing the ester group in the said diester.

  一种制备光学活性顺式-1,3-二苄六氢-1 H-呋喃并[3,4-d]咪唑-2,4-二酮的工艺，其式如下 其中星号(*)表示不对称碳，Bzl表示苄基，3a-和6a-位为顺式构型，包括选择性还原式中的光学活性顺式咪唑烷二羧酸单酯： 其中 R 为 C1-C6 烷基，Bzl 如上定义，在上述单酯中的羧基和烷氧羰基中的任一基团上用还原剂还原，然后环化，上述单酯是通过水解式如下的顺式咪唑烷二羧酸二酯得到的： 其中 R 和 Bzl 分别如上文所定义，使用一种能水解上述二酯中酯基的酶材料。
• A method for preparing optically active half esters
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0220435A1

  公开（公告）日：1987-05-06

  A method for the preparation of an optically active (4S,5R)-cis-1,3-dibenzyl-5-methoxy- or ethoxycarbonyl-2- oxoimidazolidine-4-carboxylic acid (Ia') or (4R,5S)-cis-1,3-dibenzyl-5-methoxy- or ethoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (Ib'), comprising preferentially crystallizing (la') or (Ib') from a supersaturated solution where (Ia') and Ib') are copresent in the presence of crystals of the same type of optically active half ester as that to be crystallized is disclosed.

  一种制备光学活性(4S,5R)-顺式-1,3-二苄基-5-甲氧基-或乙氧基羰基-2-氧代咪唑烷-4-羧酸(Ia')或(4R,5S)-顺式-1,3-二苄基-5-甲氧基-或乙氧基羰基-2-氧代咪唑烷-4-羧酸(Ib')的方法、本发明公开了(Ia')和(Ib')共存的过饱和溶液中(la')或(Ib')的结晶方法，该方法包括在与待结晶的光学活性半酯类型相同的晶体存在下，优先从该溶液中结晶出(la')或(Ib')。
• 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.
• Method of obtaining optically active half esters
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：EP0092194B1

  公开（公告）日：1987-07-08