(S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-methylbutanamido)-3-methylbutanoate | 33857-88-4

• 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: (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-methylbutanamido)-3-methylbutanoate
• 英文别名: tert-butyl (S)-1-((S)-1-hydroxy-3-methylbutan-2-ylamino)-3-methyl-1-oxobutan-2-ylcarbamate；methyl (S)-2-((S)-2-(tert-butoxycarbonylamino)-3-methylbutanamido)-3-methylbutanoate；N-(tert-butoxycarbonyl)-L-valinyl-L-valine methyl ester；N-tert-butoxycarbonyl-L-valinyl-L-valine methyl ester；N-(tert-butoxycarbonyl)-L-valyl-L-valinemethyl ester；N-tert-butoxycarbonyl L-valyl L-valine methyl ester；N-boc-l-valyl-l-valine methyl ester；methyl (2S)-3-methyl-2-[[(2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]butanoate
• CAS: 33857-88-4
• 化学式: C₁₆H₃₀N₂O₅
• 分子量: 330.425
• InChiKey: TZQHLJIYCPEEPF-RYUDHWBXSA-N

物化性质

• 熔点：
  130-131 °C
• 沸点：
  454.5±25.0 °C(Predicted)
• 密度：
  1.045±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-methylbutanamido)-3-methylbutanoate 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 缬氨酰-缬氨酸
  参考文献：
  名称：

  Synthesis of dipeptides based on valine and threonine

  摘要：

  Val-Val, Val-Thr, and Thr-Val dipeptides were synthesized using trifluoroacetyl protecting group. The optical rotations of the products were similar to those of samples synthesized using Boc protection, which indicated the absence of racemization in the course of introduction and removal of trifluoroacetyl protection.

  DOI：

  10.1134/s1070428012100065
• 作为产物：
  描述：

  1H-苯并三唑-1-基氧三吡咯烷基六氟磷酸盐 以95%的产率得到
  参考文献：
  名称：

  COSTE, J.;LE-NGUYEN, D.;CASTRO, B., TETRAHEDRON LETT. , 31,(1990) N, C. 205-208

  摘要：

  DOI：
• 作为试剂：
  描述：

  二碘甲烷 、 3,4-二氢-1-苯基萘 在 (S)-methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-methylbutanamido)-3-methylbutanoate 、 diethylzinc 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以40%的产率得到7b-Phenyl-1,1a,2,3-tetrahydrocyclopropa[a]naphthalene
  参考文献：
  名称：

  [EN] ASYMMETRIC CYCLOPROPANATION
  [FR] CYCLOPROPANATION ASYMETRIQUE

  摘要：

  公开号：

  WO2005033050A3

文献信息

• A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols
  作者：Sandip V. Jadhav、Anupam Bandyopadhyay、Sushil N. Benke、Sachitanand M. Mali、Hosahudya N. Gopi

  DOI：10.1039/c0ob01226b

  日期：——

  for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals

  一种简便，高效且无外消旋的方法，使用该方法合成N保护的β-氨基醇和肽醇N-羟基琥珀酰亚胺描述了活性酯。使用这种方法，可以高产率分离出二肽，三肽和五肽醇。分析了β-氨基醇，二肽和三肽醇的晶体构象，在三肽醇晶体中观察到了明确定义的III型β角。发现该方法与Fmoc-，Boc-和其他侧链保护基相容。
• Oxygen Alkylation of Schiff Base Derivatives of Amino Acids
  作者：Martin J. O'Donnell、Gwendolyn K. Cook、David B. Rusterholz

  DOI：10.1055/s-1991-26625

  日期：——

  Higher imine esters 1a-h and 7a-b of amino acids and dipeptides are prepared in 68-91% yield by saponification of the benzophenone Schiff base methyl esters 3a-d and 6 using phase-transfer techniques followed by O-alkylation with an alkyl halide. The procedure occurs with retention of configuration at the α-carbon except with phenylglycine derivatives.

  氨基酸和二肽的高亚胺酯1a-h和7a-b通过皂化苯甲酮席夫碱甲酯3a-d和6，采用相转移技术，随后与烷基卤进行O-烷基化，产率在68-91%之间。该过程在α-碳上保留构型，除了苯基甘氨酸衍生物外。
• Synthesis, SAR and biological studies of sugar amino acid-based almiramide analogues: N-methylation leads the way
  作者：Dipendu Das、Hina P. A. Khan、Rahul Shivahare、Suman Gupta、Jayanta Sarkar、Mohd. Imran Siddiqui、Ravi Sankar Ampapathi、Tushar Kanti Chakraborty

  DOI：10.1039/c6ob02610a

  日期：——

  Leishmania, is one of the most neglected diseases endemic in many continents posing enormous global health threats and therefore the discovery of new antileishmanial compounds is of utmost urgency. The antileishmanial activities of a library of sugar amino acid-based linear lipopeptide analogues were examined with the aim to identify potential drug candidates to treat visceral leishmaniasis. It was

  由利什曼原虫属的原生动物寄生虫引起的利什曼病是许多大陆上流行最严重的被忽视的疾病之一，对全球健康构成了巨大的威胁，因此，迫切需要发现新的动物抗疟疾化合物。检查了基于糖氨基酸的线性脂肽类似物库的抗菌活性，目的是鉴定潜在的候选药物治疗内脏利什曼病。已经发现，在合成的类似物中，大多数全甲基化的化合物在体外研究中显示出比非甲基化的类似物更强的抗巨噬细胞内变形虫的活性。SAR和NMR研究表明N的引入-甲基基团抑制了这些分子中任何转向结构的形成，从而改善了它们的活性。
• An efficient entry to highly substituted chiral 2-oxopiperazines from α-amino acids via iodocyclization
  作者：Amit Kumar Jana、Sanjit Kumar Das、Gautam Panda

  DOI：10.1016/j.tet.2012.09.109

  日期：2012.12

  A short and stereoselective route for the synthesis of 2-oxopiperazines is presented starting from different naturally abundant α-amino acids. The key synthetic steps involved amide coupling, Wittig reaction, HWE olefination, aza-Michael reaction, iodocyclization. This new pathway involving first report of iodocyclization to construct chiral substituted 2-oxopiperazines furnished final compounds in

  从不同的自然丰富的α-氨基酸开始，提出了合成2-氧代哌嗪的短而立体的选择性途径。关键的合成步骤涉及酰胺偶联，Wittig反应，HWE烯烃化，氮杂-迈克尔反应，碘环化。这个新的途径涉及首次报道的碘环化以构建手性取代的2-氧杂哌嗪，从而以高收率提供了最终化合物。
• Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis
  作者：Eléonore Morisset、Aurélien Chardon、Jacques Rouden、Jérôme Blanchet

  DOI：10.1002/ejoc.201901660

  日期：2020.1.23

  Phenylsilane as been reassed as useful coupling reagent for amides synthesis. Peptides and Weinreb amides are easily obtained under mild conditions in absence of epimzerization even with challenging substrates such as phenylglycine. Further investigation regarding the reactivity of stable acetoxysilanes supported phenylpolyacyloxysilane as key intermediate.

  苯甲硅烷被重新确定为用于酰胺合成的有用偶联剂。即使在温和的条件下，即使存在具有挑战性的底物（如苯基甘氨酸），也可以轻松地在温和条件下获得肽和Weinreb酰胺。关于稳定的乙酰氧基硅烷担载的关键中间体苯基聚酰氧基硅烷的反应性的进一步研究。