(R)-methyl 3-((tert-butoxycarbonyl)amino)-5-phenylpentanoate | 142638-92-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-methyl 3-((tert-butoxycarbonyl)amino)-5-phenylpentanoate
• 英文别名: methyl (3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoate
• CAS: 142638-92-4
• 化学式: C₁₇H₂₅NO₄
• 分子量: 307.39
• InChiKey: QLXPLYPDAYMKQG-CQSZACIVSA-N

物化性质

• 沸点：
  429.8±45.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  (R)-methyl 3-((tert-butoxycarbonyl)amino)-5-phenylpentanoate 在 吡啶 、 硫化氢 、 ammonium acetate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 三氟乙酸 、 lithium hexamethyldisilazane 、 碘甲烷 作用下， 以 二氯甲烷 为溶剂， 反应 3.7h， 生成 (2R,3R)-3-[(Biphenyl-4-carbonyl)-amino]-2-(3-carbamimidoyl-benzyl)-5-phenyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Identification and Initial Structure−Activity Relationships of a Novel Class of Nonpeptide Inhibitors of Blood Coagulation Factor Xa

  摘要：

  The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized p-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the Most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted p-alanines was also developed.

  DOI：

  10.1021/jm970482y
• 作为产物：
  描述：

  Boc-D-高苯丙氨酸 在 N-甲基吗啉 、 silver benzoate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 (R)-methyl 3-((tert-butoxycarbonyl)amino)-5-phenylpentanoate
  参考文献：
  名称：

  Identification and Initial Structure−Activity Relationships of a Novel Class of Nonpeptide Inhibitors of Blood Coagulation Factor Xa

  摘要：

  The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized p-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the Most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted p-alanines was also developed.

  DOI：

  10.1021/jm970482y

文献信息

• Catalytic Asymmetric Aziridination of α,β‐Unsaturated Aldehydes
  作者：Luca Deiana、Pawel Dziedzic、Gui‐Ling Zhao、Jan Vesely、Ismail Ibrahem、Ramon Rios、Junliang Sun、Armando Córdova

  DOI：10.1002/chem.201100042

  日期：2011.7.4

  highly enantioselective one‐pot cascade sequence based on the combination of asymmetric amine and N‐heterocyclic carbene catalysis (AHCC) is also disclosed. This one‐pot three‐component co‐catalytic transformation between α,β‐unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N‐tert‐butoxycarbonyl and N‐carbobenzyloxy‐protected β‐amino acid esters with ee values ranging

  介绍了α，β-不饱和醛高度对映选择性有机催化叠氮化的发展，范围和应用。α，β-不饱和醛的氨基催化叠氮化使β-甲酰基氮丙啶的不对称形成率高达> 19：1 dr和99％  ee。α-单取代的烯醛的氨基催化叠氮化可以高产率和高达99％ee的速率接近末端α-取代-α-甲酰基氮丙啶 。对于双取代的α，β-不饱和醛的有机催化叠氮化，转化具有很高的非对映选择性和对映选择性，并得到几乎对映体纯的β-甲酰基官能化氮丙啶产品（99％  ee）。还公开了基于不对称胺和N-杂环卡宾催化（AHCC）结合的高度对映选择性单锅级联序列。α，β不饱和醛，羟胺衍生物，和醇之间这种一锅三组分共催化转化得到相应的Ñ -叔丁氧羰基和ñ -苄酯基保护的β氨基酸酯与EE值范围从92- 99％。还讨论了所有这些催化转化的机理和立体化学。
• Enantioselective -Amino Acid Synthesis Based on Catalyzed Asymmetric Acyl Halide – Aldehyde Cyclocondensation Reactions
  作者：Scott G. Nelson、Keith L. Spencer

  DOI：10.1002/(sici)1521-3773(20000403)39:7<1323::aid-anie1323>3.0.co;2-x

  日期：2000.4.3
• Disulfonimide-Catalyzed Asymmetric Synthesis of β³-Amino Esters Directly from <i>N</i>-Boc-Amino Sulfones
  作者：Qinggang Wang、Markus Leutzsch、Manuel van Gemmeren、Benjamin List

  DOI：10.1021/ja408747m

  日期：2013.10.16

  An asymmetric Mannich reaction of silyl ketene acetals with N-Boc-amino sulfones has been developed. A chiral disulfonirnide efficiently catalyzes both the in situ generation of the corresponding N-Boc imines and the asymmetric Mannich reaction with excellent yields and enantioselectivities. Kinetic studies confirm a proposed stepwise mechanism.
• SUBSTITUTED N- (AMINOIMINOMETHYL OR AMINOMETHYL)PHENYL PROPYL AMIDES
  申请人：Aventis Pharmaceuticals Inc.

  公开号：EP0931060B1

  公开（公告）日：2009-11-25
• Identification and Initial Structure−Activity Relationships of a Novel Class of Nonpeptide Inhibitors of Blood Coagulation Factor Xa
  作者：Scott I. Klein、Mark Czekaj、Charles J. Gardner、Kevin R. Guertin、Daniel L. Cheney、Alfred P. Spada、Scott A. Bolton、Karen Brown、Dennis Colussi、Christopher L. Heran、Suzanne R. Morgan、Robert J. Leadley、Christopher T. Dunwiddie、Mark H. Perrone、Valeria Chu

  DOI：10.1021/jm970482y

  日期：1998.2.1

  The discovery and some of the basic structure-activity relationships of a series of novel nonpeptide inhibitors of blood coagulation Factor Xa is described. These inhibitors are functionalized p-alanines, exemplified by 2a. Docking experiments placing 2a in the active site of Factor Xa implied that the Most expeditious route to enhancing in vitro potency was to modify the group occupying the S3 site of the enzyme. Increasing the hydrophobic contacts between the inhibitor and the enzyme in this region led to 8, which has served as the prototype for this series. In addition, an enantioselective synthesis of these substituted p-alanines was also developed.