N-Boc-(S)-alanine-pivalic acid mixed anhydride | 209113-02-0

• 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: N-Boc-(S)-alanine-pivalic acid mixed anhydride
• 英文别名: [(2S)-2-(tert-butoxycarbonylamino)propanoyl] 2,2-dimethylpropanoate；(S)-2-tert.-butoxycarbonylamino-propionic acid-2,2-dimethylpropionic acid-anhydride；[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl] 2,2-dimethylpropanoate
• CAS: 209113-02-0
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: MWUVNQQAADCTGD-QMMMGPOBSA-N

物化性质

• 沸点：
  348.2±25.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Boc-(S)-alanine-pivalic acid mixed anhydride 在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Potent Proteasome Inhibitors Derived from the Unnatural cis-Cyclopropane Isomer of Belactosin A: Synthesis, Biological Activity, and Mode of Action

  摘要：

  The natural product belactosin A (1) with a trans-cyclopropane structure is a useful prototype compound for developing potent proteasome (core particle, CP) inhibitors. To date, 1 and its analogues are the only CP ligands that bind to both the nonprimed S1 pocket as well as the primed substrate binding channel; however, these molecules harbor a high IC50 value of more than 1 mu M. We have performed structure activity relationship studies, thereby elucidating unnatural cis-cyclopropane derivatives of 1 that exhibit high potency to primarily block the chymotrypsin-like active site of the human constitutive (cCP) and immunoproteasome (iCP). The most active compound 3e reversibly inhibits cCP and iCP similarly with an IC50 of 5.7 nM. X-ray crystallographic analysis of the yeast proteasome in complex with 3e revealed that the ligand is accommodated predominantly into the primed substrate binding channel and covalently binds to the active site threonine residue via its beta-lactone ring-opening.

  DOI：

  10.1021/jm4002296
• 作为产物：
  描述：

  三甲基乙酰氯 在 二环己胺 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 N-Boc-(S)-alanine-pivalic acid mixed anhydride
  参考文献：
  名称：

  WO2008/8327

  摘要：

  公开号：

文献信息

• Design and synthesis of florylpicoxamid, a fungicide derived from renewable raw materials
  作者：Nicholas R. Babij、Nakyen Choy、Megan A. Cismesia、David J. Couling、Nicole M. Hough、Peter L. Johnson、Jerzy Klosin、Xiaoyong Li、Yu Lu、Elizabeth O. McCusker、Kevin G. Meyer、James M. Renga、Richard B. Rogers、Kenneth E. Stockman、Nicola J. Webb、Gregory T. Whiteker、Yuanming Zhu

  DOI：10.1039/d0gc02063j

  日期：——

  4-trisubstituted pyridine motif from furfural further increased the renewable carbon content of the active ingredient to nearly 50%. Throughout process development, improved reaction conditions and industrially-preferred alternatives were identified to replace hazardous reagents for key transformations. In all, the holistic use of Green Chemistry principles in the design and synthesis of florylpicoxamid will

  广谱杀菌剂florylpicoxamid的设计和合成体现了多种绿色化学原理。该活性成分经过战略性设计，可提供最大的生物活性并在施用后迅速降解，以最大程度地降低其对环境的影响。与许多手性农作物保护化学品不同，氟吡草胺是作为单一的立体异构体开发的，目的是最大程度地减少田间应用中该产品的剂量率，并避免其活性较低的立体异构体对环境造成的任何潜在负担。幸运的是，天然产物启发的活性成分中最有效的立体异构体可以衍生自乳酸和丙氨酸的天然对映体。绿色化学原理还被用于改善最初为结构-活性关系研究而开发的合成途径，导致聚合的立体选择性合成更可持续和更具成本效益。精简2第一种生成途径减少了保护基的使用，并使用了更安全的反应溶剂。从糠醛向2,3,4-三取代吡啶基序的新合成序列的开发进一步将活性成分的可再生碳含量提高到近50％。在整个工艺开发过程中，确定了改善的反应条件和行业首选的替代品，以替代用于关键转化的危险试剂
• An Easy and Fast Conversion ofN2-[(tert-Butoxy)carbonyl]-L-amino Acids to Corresponding Amino-aldehydes
  作者：Pavol Zlatoidsky

  DOI：10.1002/hlca.19940770220

  日期：1994.3.23

  A new method for the preparation of N2-[(tert-butoxy)carbonyl]-L-amino-aldehydes from N2-[(tert-butoxy)carbonyl]-L-amino acids based on reduction of mixed anhydrides with LiAl(t-BuO)3H is described.

  用于制备的新方法Ñ 2 - [（叔丁氧基）羰基] -L-氨基醛从Ñ 2 - [（叔丁氧基）羰基] -L-氨基基于与减少的LiAl混合酸酐的酸（吨-BuO）3 H的说明。
• Process and intermediates for the synthesis of 2-(quinolin-5-yl)-4,5 disubstituted-azole derivatives
  申请人：Cutarelli D. Timothy

  公开号：US20080045718A1

  公开（公告）日：2008-02-21

  This application discloses a novel process to synthesize 2-(Quinolin-5yo)-4,5-Disubstituted-Azole derivatives, which may be used, for example, as PDE IV inhibitor compounds in pharmaceutical preparations.

  这项申请揭示了一种合成2-(喹啉-5-基)-4,5-二取代-咪唑衍生物的新工艺，该衍生物可以用作制药制剂中的PDE IV抑制剂化合物。
• Process for the preparation of mixed anhydrides
  申请人：——

  公开号：US20020077481A1

  公开（公告）日：2002-06-20

  The present invention is concerned with an improved process for the manufacture of mixed anhydrides. The process comprises adding an adjuvant base to a mixture of acid and reactive acid derivative. It is especially suitable for use in the synthesis of peptides and/or for the manufacture of pharmaceutically active substances or corresponding intermediates.

  本发明涉及一种改进的混合酸酐制造过程。该过程包括向酸和反应性酸衍生物的混合物中添加辅助碱。它特别适用于合成肽和/或制造药用活性物质或相应中间体。
• Asymmetric Synthesis of α-Methyl α-Amino Acids through Diastereoselective Alkylation under Mild Reaction Conditions of an Iminic Alanine Template with a 1,2,3,6-Tetrahydro-2-pyrazinone Structure
  作者：Carmen Nájera、Tomás Abellán、José M. Sansano

  DOI：10.1002/1099-0690(200008)2000:15<2809::aid-ejoc2809>3.0.co;2-x

  日期：2000.8

  room temperature by: a) activated alkyl halides under solid-liquid PTC conditions, b) non-activated alkyl halides with organic bases, c) electrophilic olefins employing both solid−liquid PTC conditions and organic bases, and d) allylic carbonates by means of palladium catalysis under neutral conditions. Enantiomerically pure (S)-α-methyl α-amino acids 8 are obtained by hydrolysis of the alkylated pyrazinones

  从（R）-缬氨酸和（S）-丙氨酸获得的（6 R）-6-异丙基-3-甲基-5-苯基-1,2,3,6-四氢-2-吡嗪酮在以下位置高度非对映选择性烷基化室温：a）在固液PTC条件下的活化烷基卤化物； b）具有有机碱的非活化烷基卤化物； c）在固液PTC条件和有机碱下均具有亲电性的烯烃； d）通过以下方式得到烯丙基碳酸酯：钯在中性条件下催化。对映体纯的（S）-α-甲基α-氨基酸8是通过烷基化的吡嗪酮的水解得到的。