N-trichloroethoxycarbonyl-L-valine | 78221-33-7

• 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-trichloroethoxycarbonyl-L-valine
• 英文别名: Troc-Val；Tec-Val-OH；Troc-L-valine；((2,2,2-trichloroethoxy)carbonyl)-L-valine；(S)-3-methyl-2-[(2,2,2-trichloroethoxy)carbonylamino]butyric acid；(2S)-3-Methyl-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}butanoic acid；(2S)-3-methyl-2-(2,2,2-trichloroethoxycarbonylamino)butanoic acid
• CAS: 78221-33-7
• 化学式: C₈H₁₂Cl₃NO₄
• 分子量: 292.547
• InChiKey: QWBAEXAXGICBAB-YFKPBYRVSA-N

物化性质

• 熔点：
  -4.1 °C
• 沸点：
  392.2±42.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  N-trichloroethoxycarbonyl-L-valine 在 盐酸 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 33.0h， 生成 利托那韦
  参考文献：
  名称：

  一种利托那韦的制备方法

  摘要：

  本发明涉及医药技术领域，具体是一种利托那韦的制备方法。本发明通过以（2‑异丙基噻唑‑4‑基）‑氮‑甲基甲胺为原料，经过三步反应合成利托那韦。通过氯甲酸三氯乙醇酯构建脲键，使用便宜易得的对甲苯磺酰氯做为酰胺的缩合剂，高收率的合成了利托那韦，其收率为79%，与现有制备方法相比，具有成本较低，绿色环保，易于规模化生产等优点，具有较好的应用前景。

  公开号：

  CN109369562A
• 作为产物：
  描述：

  L-缬氨酸 、 氯甲酸-2,2,2-三氯乙酯 在 sodium hydroxide 作用下， 以72%的产率得到N-trichloroethoxycarbonyl-L-valine
  参考文献：
  名称：

  N-2,2,2-Trichloroethoxycarbonyl-L-amino Acids

  摘要：

  DOI：

  10.1055/s-1981-29408

文献信息

• Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates
  作者：Alenka Paquet

  DOI：10.1139/v82-146

  日期：1982.4.15

  9-Fluorenylmethyl succinimidyl, pentachlorophenyl, and benzotriazole-1-yl carbonates were prepared and their reactivity with L-serine and L-serine benzyl ester was compared. The most efficient reagent, 9-fluorenylmethyl succinimidyl carbonate, was used for the preparation of 9-fluorenylmethyloxycarbonyl derivatives of other hydroxyamino acids and hydroxyamino acid esters in high yields. The use of trichloroethyl and benzyl succinimidyl carbonates for an efficient conversion of hydroxyamino acids and their esters into the corresponding N-trichloroethoxycarbonyl and benzyloxycarbonyl derivatives is described.

  9-氟基甲基琥珀酰亚胺基、五氯苯基和苯并三唑-1-基碳酸酯被制备，并与L-丝氨酸和L-丝氨酸苄酯的反应性进行了比较。最有效的试剂，9-氟基甲基琥珀酰亚胺基碳酸酯，被用于高产率制备其他羟基氨基酸和羟基氨基酸酯的9-氟基甲氧羰基衍生物。描述了三氯乙基和苄基琥珀酰亚胺基碳酸酯的使用，用于将羟基氨基酸及其酯有效转化为相应的N-三氯乙氧羰基和苄氧羰基衍生物。
• Simplified beta-glycosylation of peptides
  作者：Yonglian Zhang、Spencer Knapp

  DOI：10.1016/j.tet.2018.04.082

  日期：2018.6

  A simple and effective activating system for S-phenyl thioglycosides, namely N-iodosuccinimide and catalytic copper(I) triflate, promotes beta-O-glycosylation at the serine and threonine hydroxyls of “mono-,” di-, and tripeptides. The same activator combination promotes carboxamide beta-N-glycosylation of asparagine-containing mono-, di, and tri-peptides, as well as a nucleoside carboxamide and a sulfonamide

  一个简单而有效的S-苯基硫糖苷活化系统，即N-碘琥珀酰亚胺和催化三氟甲磺酸铜（I），可促进“单肽”，“二肽”和“三肽”的丝氨酸和苏氨酸羟基上的β-O-糖基化。相同的活化剂组合可促进含有天冬酰胺的单肽，二肽和三肽的羧酰胺β-​​N-糖基化，以及核苷羧酰胺和磺酰胺。三氟甲磺酸铜（I）方法的一个重要特征是，很大程度上避免了不希望的酰胺O-糖基化。对于两组重要的生物重要受体位点（H O –和–CO N H 2），β-GlcNAc等效供体被证明可以有效地提供联系。已基于整体氢解作用开发了简化的脱保护序列，该序列可顺利产生亲本糖肽。生物蛋白的核心糖肽区域Ñ -glycosylation，由N表示4 - （β- Ñ乙酰基d-2葡糖）-Asp -甘氨酸-苏氨酸-OH，已经在溶液中制备，纯化，表征为完全脱保护的（单）糖基化三肽。
• The Synthesis of a Heavy-Atom Derivative of Gramicidin S (GS), [D-Phe(4-Br)^4,4′]-GS, by a Novel Method
  作者：Saburo Aimoto

  DOI：10.1246/bcsj.61.2220

  日期：1988.6

  A new approach for the preparation of cyclic peptides was successfully applied to the synthesis of cyclo(–Val–Orn–Leu–d–Phe(4-Br)–Pro–Val–Orn–Leu–d–Phe (4-Br)–Pro–) ([d–Phe(4-Br)4,4′]-GS). [d–Phe(4-Br)4,4′]–GS showing antibacterial activity was obtained as crystals.

  一种制备环肽的新方法被成功应用于合成环(-Val-Orn-Leu-d-Phe(4-Br)-Pro-Val-Orn-Leu-d-Phe (4-Br)-Pro-)（[d-Phe(4-Br)4,4′]-GS）。得到的[d-Phe(4-Br)4,4′]-GS 为晶体，具有抗菌活性。
• Synthesis and in vitro evaluation of new derivatives of 2-substituted-6-fluorobenzo[d]thiazoles as cholinesterase inhibitors
  作者：Aleš Imramovský、Vladimír Pejchal、Šárka Štěpánková、Katarína Vorčáková、Josef Jampílek、Ján Vančo、Petr Šimůnek、Karel Královec、Lenka Brůčková、Jana Mandíková、František Trejtnar

  DOI：10.1016/j.bmc.2013.01.052

  日期：2013.4

  A series of novel cholinesterase inhibitors based on 2-substituted 6-fluorobenzo[d]thiazole were synthesised and characterised by IR, H-1, C-13 and F-19 NMR spectroscopy and HRMS. Purity was checked by elemental analyses. The novel carbamates were tested for their ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The toxicity of the most active compounds was investigated using a standard in vitro test with HepG2 cells, and the ratio between biological activity and toxicity was determined. In addition, the toxicity of the most active compounds was evaluated against MCF7 cells using the xCELLigence system. Structure-activity relationships reflecting the dependence of cholinesterase inhibitors on the lipophilicity of the compounds as well as on the Taft polar and steric substituent constants are discussed. The specific orientation of the inhibitors in the binding site of acetylcholinesterase was determined using molecular docking of the most active compound. (C) 2013 Elsevier Ltd. All rights reserved.
• Paquet, Alenka; Chen, Francis M. F.; Benoiton, N. Leo, Canadian Journal of Chemistry, 1984, vol. 62, p. 1335 - 1338
  作者：Paquet, Alenka、Chen, Francis M. F.、Benoiton, N. Leo

  DOI：——

  日期：——