(3R,4S)-4-methyl-3-({[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid | 872423-93-3

• 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: (3R,4S)-4-methyl-3-({[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid
• 英文别名: (3R,4S)-3-(benzyloxycarbonylamino)-4-methylhexanoic acid；Z-L-β-homoisoleucine；(3R,4S)-3-{[(Benzyloxy)carbonyl]amino}-4-methylhexanoic acid；(3R,4S)-4-methyl-3-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 872423-93-3
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: YBQVXOLUUAILCJ-WCQYABFASA-N

物化性质

• 熔点：
  102-106 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  457.7±38.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-4-methyl-3-({[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid 在 camphor-10-sulfonic acid 、 溶剂黄146 三乙基硅烷 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  1,3-恶唑烷酮-5-酮和1,3-恶唑烷酮-6-酮由二十种常见的α-氨基酸合成N-甲基β-氨基酸的有效方法

  摘要：

  应用N-甲基β-氨基酸通常是潜在合成具有生物活性的修饰的肽和其他寡聚体的应用。先前的工作强调了1，3-恶唑烷-5-酮的还原裂解以合成N-甲基α-氨基酸。从α-氨基酸开始，使用两种方法来制备相应的N-甲基β-氨基酸。首先，α -氨基酸转化为Ñ甲基α -氨基酸由所谓的“-1,3-恶唑-5-酮的策略”，将它们再由同系阿恩特-艾斯特方法，得到Ñ-protected Ñ -甲基β -氨基酸选自20种常见衍生α -氨基酸。这些化合物的制备产率为23–57％（相对于N-甲基α-氨基酸）。在第二种方法中，可以通过Arndt–Eistert方法将12个N保护的α-氨基酸直接同源，然后将所得的β-氨基酸以30–45％的产率转化为1,3-恶二嗪-6-酮。 。最后，还原裂解以41–63％的收率提供了所需的N-甲基β-氨基酸。

  DOI：

  10.1002/hlca.200690235
• 作为产物：
  描述：

  isoleucine 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醚 、 水 为溶剂， 反应 6.25h， 生成 (3R,4S)-4-methyl-3-({[(phenylmethyl)oxy]carbonyl}amino)hexanoic acid
  参考文献：
  名称：

  Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

  摘要：

  Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.098

文献信息

• Isoselenocyanates derived from Boc/Z-amino acids: synthesis, isolation, characterization, and application to the efficient synthesis of unsymmetrical selenoureas and selenoureidopeptidomimetics
  作者：Gundala Chennakrishnareddy、Govindappa Nagendra、Hosahalli P. Hemantha、Ushati Das、Tayur N. Guru Row、Vommina V. Sureshbabu

  DOI：10.1016/j.tet.2010.06.082

  日期：2010.8

  Isoselenocyanates derived from Boc/Z-amino acids are prepared by the reaction of the corresponding isonitriles with selenium powder in presence of triethylamine at reflux. The utility of these new classes of isoselenocyanates in the preparation of selenoureidodipeptidomimetics possessing both amino as well as carboxy termini has been accomplished. The H-1 NMR analysis confirmed that the protocol involving the conversion of isonitriles to isoselenocyanates and their use as coupling agents in assembling selenour-eido derivatives is free from racemization. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step
  作者：Maité Sylla-Iyarreta Veitía、Pierre Louis Brun、Pierre Jorda、Annie Falguières、Clotilde Ferroud

  DOI：10.1016/j.tetasy.2009.07.045

  日期：2009.9

  Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected beta(3)-amino nitriles into their corresponding N-protected beta(3)-amino acids.The biotransformations were obtained in different proportions depending oil the nitrilase involved The best hydrolysis results were achieved for the N-Cbz-beta(3)-amino nitrile from i-alanine using the NIT-107, in a phosphate buffer at 0 05 M However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide beta(3)-amino nitriles. Two simple and efficient procedures to prepare the beta(3)-amino nitriles from their analogous alpha-amino acids are described Thirty four new substances were synthesized and characterized over the course of this work. (C) 2009 Elsevier Ltd All rights reserved
• Total synthesis of Leucinostatin D
  作者：Shigeru Kuwata、Akihiro Nakanishi、Takashi Yamada、Toshifumi Miyazawa

  DOI：10.1016/s0040-4039(00)60915-2

  日期：1992.11

  Peptide antibiotic, Leucinostatin D, was synthesized by stepwise elongation method, starting from beta-alanine t-bytyl ester. Z-octapeptide ester was converted to amide derivative and finally coupled with (4S,E)-4-methylhex-2-enoyl-L-4-methylproline.
• Exceptionally Simple Homologation of Protected α‐ to β‐Amino Acids in the Presence of Silica Gel
  作者：Karen Koch、Joachim Podlech

  DOI：10.1080/00397910500290466

  日期：2005.11.1

  The Wolff rearrangement of alpha-amino acid-derived diazoketones is simply achieved by gentle warming in a ethyl acetate/silica gel slurry containing catalytic amounts of silver trifluoroacetate. Without workup (not counting filtration and evaporation) the protected beta-amino acids are obtained in high yields (92-97%) without significant impurities. This variation avoids the laborious workup after a conventional silver-catalyzed Wolff rearrangement. This method can be similarly applied to the synthesis of beta-amino acid methyl esters when methanol is used as solvent. No reaction occurs without silica gel.
• Diastereoselective Synthesis of α-Methyl and α-Hydroxy-β-Amino Acids via 4-Substituted-1,3-Oxazinan-6-ones
  作者：Brad E. Sleebs、Andrew B. Hughes

  DOI：10.1021/jo0700326

  日期：2007.4.1

  1,3-Oxazinan-6-ones have been utilized in a series of enolate reactions to produce 5-hydroxy and 5-alkyl-4-substituted-1,3-oxazinan-6-ones with excellent trans diastereoselectivity. Highlighting the versatility of the oxazinanone, a number of transformations were performed to produce a variety of protected N-H and N-methyl alpha-hydroxy- and alpha-methyl-beta-amino acids.