[9-fluorenylmethoxycarbonyl]-2-vinylglycine methyl ester | 500872-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: [9-fluorenylmethoxycarbonyl]-2-vinylglycine methyl ester
• 英文别名: N-Fmoc-2S-vinylglycine methyl ester；Fmoc-VGly-OMe；(S)-Methyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)but-3-enoate；methyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)but-3-enoate
• CAS: 500872-35-5
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: ALGZRVLGHPUXMV-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [9-fluorenylmethoxycarbonyl]-2-vinylglycine methyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 (S)-N-Fmoc-乙烯基甘氨酸
  参考文献：
  名称：

  A modular, general and enantiospecific strategy for the synthesis of CVS 1778 analogs: inhibitors of factor Xa

  摘要：

  A modular synthetic route has been developed for the synthesis of a series of complex benzalactams which are potent inhibitors of factor Xa. The route produces fused benzalactams of varying ring size via a key-step ring-closing metathesis reaction. The route also facilitates the synthesis of discrete enantiomers using readily available commercial building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01924-x
• 作为产物：
  描述：

  Fmoc-L-Met-OMe 在 sodium periodate 作用下， 以 甲醇 、 水 、 xylene 为溶剂， 反应 92.0h， 生成 [9-fluorenylmethoxycarbonyl]-2-vinylglycine methyl ester
  参考文献：
  名称：

  A modular, general and enantiospecific strategy for the synthesis of CVS 1778 analogs: inhibitors of factor Xa

  摘要：

  A modular synthetic route has been developed for the synthesis of a series of complex benzalactams which are potent inhibitors of factor Xa. The route produces fused benzalactams of varying ring size via a key-step ring-closing metathesis reaction. The route also facilitates the synthesis of discrete enantiomers using readily available commercial building blocks. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01924-x

文献信息

• [EN] PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS<br/>[FR] PROCÉDÉS DE SYNTHÈSE DE GAMMA-LACTAMES AMINO-SUBSTITUÉS
  申请人：VALORISATION RECH SOC EN COMMA

  公开号：WO2010105367A1

  公开（公告）日：2010-09-23

  The present application describes general process for the preparation of amino-substitued gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substitued gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.

  本申请描述了一般的氨基取代γ-内酰胺的制备过程，涉及到通式(I)和(VI)的合成子与胺的反应。这些过程适用于固相合成技术，因此可以有效地将氨基取代γ-内酰胺并入各种结构支架中，特别是肽类结构。
• A novel dipeptidomimetic containing a cyclic threonine
  作者：Frank Sicherl、Tommaso Cupido、Fernando Albericio

  DOI：10.1039/b915220b

  日期：——

  An efficient and simple two-step procedure for the formation of hydroxy-Freidinger lactams is presented. The methodology allows assembly of the cyclic threonine motif (cThr) in solution and on solid support during conventional peptide synthesis.

  提出了一种有效且简单的两步程序，用于形成羟基-弗雷丁格内酰胺。该方法可以在常规肽合成过程中在溶液中和固体支持物上组装环状苏氨酸基序（cThr）。
• Continuous-flow thermolysis for the preparation of vinylglycine derivatives
  作者：Nicolas Lamborelle、Justine F. Simon、André Luxen、Jean-Christophe M. Monbaliu

  DOI：10.1039/c5ob02036k

  日期：——

  sulfoxide elimination was carried out under continuous-flow conditions in a mesofluidic thermolysis reactor. The design of the reactor enabled accurate control of reaction time and conditions, affording a convenient scale-independent procedure for the production of N,C-protected vinylglycine derivatives. Thermolysis at 270 °C under 1000 psi of pressure in superheated toluene enabled typical daily outputs

  顺式亚砜消除在中射流热解反应器的连续流动条件下进行。反应器的设计能够精确控制反应时间和条件，为制备N，C保护的乙烯基甘氨酸衍生物提供了与规模无关的便捷程序。在270°C和1000 psi的压力下在过热的甲苯中进行热解，典型的每日产量为11至46 g / day，具有出色的选择性和ee（> 97％）。根据计算研究，研究了各种竞争反应途径并进行了合理化。
• A program for ligation at threonine sites: application to the controlled total synthesis of glycopeptides
  作者：Jin Chen、Ping Wang、Jianglong Zhu、Qian Wan、Samuel J. Danishefsky

  DOI：10.1016/j.tet.2010.01.067

  日期：2010.3

  A method by which to accomplish formal threonine ligation has been developed. The method accomplishes ligations of two peptide domains. We have also demonstrated the ability to successfully ligate two independent glycopeptide domains.

  已经开发了一种完成正式苏氨酸连接的方法。该方法完成了两个肽域的连接。我们还展示了成功连接两个独立糖肽域的能力。
• PROCESSES FOR PREPARING AMINO-SUBSTITUTED GAMMA-LACTAMS
  申请人：Lubell William

  公开号：US20120101257A1

  公开（公告）日：2012-04-26

  The present application describes general process for the preparation of amino-substituted gamma-lactams involving the reaction of synthons of the general Formulae (I) and (VI): with amines. The processes are amenable to solid phase synthetic techniques and therefore allow the efficient incorporation of amino-substituted gamma-lactams into a wide variety of structural scaffolds, including, in particular peptides.

  该申请书描述了一种制备氨基取代的γ-内酰胺的通用过程，包括将通式(I)和(VI)的合成物与胺反应。这些过程适用于固相合成技术，因此可以有效地将氨基取代的γ-内酰胺纳入各种结构支架中，特别是肽中。