(2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(p-toluenesulfonyloxymethyl)-pyrrolidine | 792916-37-1

• 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: (2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(p-toluenesulfonyloxymethyl)-pyrrolidine
• 英文别名: benzyl (4R)-hydroxy-(2S)-(p-toluenesulfonyloxymethyl)pyrrolidine-1-carboxylate；benzyl (2S,4R)-4-hydroxy-2-[(4-methylphenyl)sulfonyloxymethyl]pyrrolidine-1-carboxylate
• CAS: 792916-37-1
• 化学式: C₂₀H₂₃NO₆S
• 分子量: 405.472
• InChiKey: PSYWHSIGZZVQGR-ZWKOTPCHSA-N

物化性质

• 沸点：
  589.4±50.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(p-toluenesulfonyloxymethyl)-pyrrolidine 在 镍 sodium azide 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 20.0~55.0 ℃ 、275.79 kPa 条件下， 反应 19.5h， 生成 (2S,4R)-N1-(benzyloxycarbonyl)-2-(tert-butyloxycarbonylaminomethyl)-4-hydroxy-pyrrolidine
  参考文献：
  名称：

  Backbone extended pyrrolidine PNA (bepPNA): a chiral PNA for selective RNA recognition

  摘要：

  Synthesis of cationic, chiral PNA analogues with an extra atom in the backbone (bepPNA) is reported. The (2S,4S) geometry of the pyrrolidine ring, and an additional carbon atom in the backbone of homopyrimidine-bepPNAs resulted in the optimization of the inter-nucleobase distance, such that selective binding to complementary RNA over DNA was observed in the triplex mode. It was evident from circular dichroism studies that oligomers with mixed aminoethylglycyl-bep (aeg-bep) repeating units, and also bepPNA with homogeneous backbone attained structures quite different from those of aegPNA(2):RNA/DNA complexes. The bepPNA. when incorporated in a duplex forming mixed purine-pyrimidine sequence, also showed a preference for binding complementary RNA over DNA. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.002
• 作为产物：
  描述：

  Cbz-L-羟脯氨酸 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 15.0h， 生成 (2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(p-toluenesulfonyloxymethyl)-pyrrolidine
  参考文献：
  名称：

  Backbone extended pyrrolidine PNA (bepPNA): a chiral PNA for selective RNA recognition

  摘要：

  Synthesis of cationic, chiral PNA analogues with an extra atom in the backbone (bepPNA) is reported. The (2S,4S) geometry of the pyrrolidine ring, and an additional carbon atom in the backbone of homopyrimidine-bepPNAs resulted in the optimization of the inter-nucleobase distance, such that selective binding to complementary RNA over DNA was observed in the triplex mode. It was evident from circular dichroism studies that oligomers with mixed aminoethylglycyl-bep (aeg-bep) repeating units, and also bepPNA with homogeneous backbone attained structures quite different from those of aegPNA(2):RNA/DNA complexes. The bepPNA. when incorporated in a duplex forming mixed purine-pyrimidine sequence, also showed a preference for binding complementary RNA over DNA. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.002

文献信息

• Backbone-extended pyrrolidine peptide nucleic acids (bepPNA): design, synthesis and DNA/RNA binding studies
  作者：T. Govindaraju、Vaijayanti A. Kumar

  DOI：10.1039/b413542c

  日期：——

  One-carbon extended conformationally constrained pyrrolidine PNA monomer (bepPNA) has been synthesized, incorporated into PNA sequences at predefined positions, and showed selective RNA binding properties.

  一碳扩展构象约束的吡咯烷PNA单体（bepPNA）已被合成，并在预定位置掺入PNA序列，并显示出选择性的RNA结合特性。
• Process for producing pyrrolidine derivative
  申请人：Nakayama Atsushi

  公开号：US20070105935A1

  公开（公告）日：2007-05-10

  This invention provides an industrially useful process for producing 1,4-transcyclohexanecarboxylic acid derivative (1) which has excellent VLA-4 inhibitory action and safety, and an intermediate which is useful in such method. More particularly, this invention relates to a process for converting a compound of formula (I) into a compound of formula (VI) by the reaction scheme:

  该发明提供了一种工业上有用的制备1,4-顺环己烷羧酸衍生物（1）的方法，该方法具有出色的VLA-4抑制作用和安全性，并且提供了一种在该方法中有用的中间体。更具体地说，该发明涉及通过反应方案将式（I）化合物转化为式（VI）化合物的方法：
• Synthesis of<i>trans</i>-L/D-2-(Tert-butoxycarbonyl- aminomethyl)-4-(thymin-1-yl) Pyrrolidin-1-yl Acetic Acid
  作者：Vaijayanti A. Kumar、Meena

  DOI：10.1081/ncn-120022947

  日期：2003.10

  To delineate the binding preferences of stereochemically divergent pyrrolidine PNAs, synthesis of all four diastreomeric monomers of I and the systematic complexation studies of the resultant PNAs with complementary DNA/RNA is essential. We herein report the synthesis of trans-L/D-2-(tert-butoxycarbonyl-aminomethyl)-4-(thymin-1-yl) pyrrolidin-1-yl acetic acids I, their incorporation in PNA oligomers and DNA binding studies will be presented.
• EP1623975
  申请人：——

  公开号：——

  公开（公告）日：——
• US7345179B2
  申请人：——

  公开号：US7345179B2

  公开（公告）日：2008-03-18