N-benzyl-N-tert-butoxycarbonylphenylalanine methyl ester | 145654-99-5

• 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-benzyl-N-tert-butoxycarbonylphenylalanine methyl ester
• 英文别名: (S)-2-(benzyl-tert-butoxycarbonyl-amino)-3-phenyl-propionic acid methyl ester；(S)-methyl 2-(benzyl(tert-butoxycarbonyl)amino)-3-phenylpropanoate；methyl (2S)-2-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-phenylpropanoate
• CAS: 145654-99-5
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: FTLPJVJPVJQZCB-IBGZPJMESA-N

物化性质

• 沸点：
  484.1±44.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-tert-butoxycarbonylphenylalanine methyl ester 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 (1'R,2'S)-2-<2'-<(N-tert-Butoxycarbonyl)benzylamino>-1'-<(tert-butyldimethylsilyl)oxy>-3'-phenylpropyl>-1,3-thiazole
  参考文献：
  名称：

  Homologation of L-phenylalanine to ketomethylene and hydroxyethylene dipeptide isosteres via 2-thiazolyl amino ketone intermediate

  摘要：

  A highly efficient route is presented for the synthesis of N-protected isosteric dipeptides Phepsi[COCH2]Gly and Phepsi[CH(OH)CH2]Phe from L-phenylalanine through 2-thiazolyl alpha-amino ketone and delta-amino-gamma-hydroxy-(E)-alpha,beta-enoate derivatives as key intermediates.

  DOI：

  10.1016/s0040-4039(00)60888-2
• 作为产物：
  描述：

  (S)-2-(benzylidene-amino)-3-phenyl-propionic acid methyl ester 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 18.5h， 生成 N-benzyl-N-tert-butoxycarbonylphenylalanine methyl ester
  参考文献：
  名称：

  2-Thiazolyl α-Amino Ketones: A New Class of Reactive Intermediates for the Stereocontrolled Synthesis of Unusual Amino Acids

  摘要：

  描述了四种α-氨基酸（L-苯丙氨酸、L-亮氨酸、L-苏氨酸和L-丝氨酸）的噻唑基单碳同源化，生成相应的α-羟基β-氨基醛和酸，且在Cα上具有两种构型。该方法论涉及以下关键操作：（i）将α-氨基酯转化为2-噻唑基α-氨基酮；（ii）对酮羰基进行立体选择性还原，生成syn或anti的α,β-氨基醇；（iii）从噻唑环中释放醛；（iv）将醛氧化为羧酸。由于操作（i）的一些限制，该方法论仅部分应用于L-苯甘氨酸。

  DOI：

  10.1055/s-1993-26021

文献信息

• A Practical Total Synthesis of Hapalosin, a 12-Membered Cyclic Depsipeptide with Multidrug Resistance-Reversing Activity, by Employing Improved Segment Coupling and Macrolactonization
  作者：Claudio Palomo、Mikel Oiarbide、Jesús M. García、Alberto González、Raquel Pazos、José M. Odriozola、Patricia Bañuelos、Mónica Tello、Anthony Linden

  DOI：10.1021/jo0497499

  日期：2004.6.1

  A practical total synthesis of hapalosin, a compound with multidrug resistance-reversing activity, has been carried out using an unprecedented macrolactonization strategy. One of the features of the new approach is the straightforward and fully stereocontrolled access to the key γ-amino β-hydroxy carboxylic acid subunit via an efficient acetate aldol addition reaction with N-methyl α-aminoaldehydes

  已使用一种前所未有的大内酯化策略进行了一种具有多药耐药性逆转活性的化合物哈帕洛辛的实际全合成。新方法的特点之一是通过与N的高效乙酸羟醛加成反应，可以直接且完全立体控制对关键的γ-氨基β-羟基羧酸亚基的访问-甲基α-氨基醛，它依赖于樟脑衍生的手性乙酸锂烯醇盐试剂。研究了该醛醇缩合反应的范围，并说明了其在其他结构相关，生物学相关化合物的合成中的潜在应用。显着地，所得γ-氨基羟醛加合物中的手性束缚剂在空间上保护羰基，从而避免了在氨基脱保护和随后的链段偶联过程中分子内环化。在成功的片段偶联和手性助剂的顺畅，干净的释放之后，基于两个反应位点均双重激活的原理，应用了一种新的大环内酯化方案，从而以前所未有的化学效率产生了12元的大环内酯类蛇毒蛋白。
• Memory of Chirality Concept in Asymmetric Intermolecular Michael Addition of α-Amino Ester Enolates to Enones and Nitroalkenes
  作者：Vadlamuri Veeraswamy、Gaurav Goswami、Satobhisha Mukherjee、Koena Ghosh、Manik Lal Saha、Arunava Sengupta、Manas K. Ghorai

  DOI：10.1021/acs.joc.7b02315

  日期：2018.2.2

  A highly stereoselective asymmetric intermolecular conjugate addition of α-amino ester derivatives to cyclic enones via the memory of chirality (MOC) concept in high yields with excellent diastereo- and enantioselectivity (dr >99:1, up to 99% ee) is reported. The applicability and the generality of the strategy was demonstrated by its further exploration to acyclic α,β-unsaturated ketone and aromatic

  据报道，通过手性（MOC）概念的记忆，α-氨基酯衍生物高度立体选择性地不对称分子间共轭加成至环状烯酮，具有高收率，具有出色的非对映选择性和对映选择性（dr> 99：1，可达99％ee）。该策略对无环α，β-不饱和酮和芳族硝基烯烃的进一步探索证明了该策略的适用性和普遍性，导致形成了δ-酮-α-氨基酯衍生物和γ-硝基-α-氨基酯衍生物，分别具有出色的ee和dr。
• Chelation- and Non-chelation-Controlled Addition of 2-(Trimethylsilyl)thiazole to .alpha.-Amino Aldehydes: Stereoselective Synthesis of the .beta.-Amino-.alpha.-hydroxy Aldehyde Intermediate for the Preparation of the Human Immunodeficiency Virus Proteinase Inhibitor Ro 31-8959
  作者：Alessandro Dondoni、Daniela Perrone、Pedro Merino

  DOI：10.1021/jo00129a057

  日期：1995.12
• Scope and limitations of the alkylidene carbene 1,5-CH insertion reactions of α-amino acid-derived substrates
  作者：Renameditswe Mapitse、Christopher J Hayes

  DOI：10.1016/s0040-4039(02)00585-3

  日期：2002.5

  A range of alpha-amino acid-derived cyclisation precursors were synthesised from suitably protected alpha-amino esters, via a Dibal-H/Wittig/catalytic hydrogenation strategy and each of these was subjected to alkylidene carbene-forming conditions (lithio(trimethylsilyl)diazomethane, THF). The cyclisations proceeded in poor to good yield, with the best cyclisations occurring to produce spirocyclic products. (C) 2002 Published by Elsevier Science Ltd.
• A stereodivergent cascade imine→azomethine ylide→1,3-dipolar cycloadditive approach to α-chiral pyrrolidines
  作者：Philip Garner、H. Ümit Kaniskan

  DOI：10.1016/j.tetlet.2005.05.119

  日期：2005.8

  Stereodivergent [3+2] cycloadditions of chiral alpha-amino azoinethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and alpha-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics. (c) 2005 Elsevier Ltd. All rights reserved.