(S)-2-((4-methylphenyl)sulfonamido)-3-(4-(tosyloxy)phenyl)propanoic acid | 13504-90-0

• 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)-2-((4-methylphenyl)sulfonamido)-3-(4-(tosyloxy)phenyl)propanoic acid
• 英文别名: N,O-ditosyl-tyrosine；(2S)-2-[(4-methylphenyl)sulfonylamino]-3-[4-(4-methylphenyl)sulfonyloxyphenyl]propanoic acid
• CAS: 13504-90-0
• 化学式: C₂₃H₂₃NO₇S₂
• 分子量: 489.57
• InChiKey: ZOVOOOBCFIWCAP-QFIPXVFZSA-N

物化性质

• 沸点：
  697.1±65.0 °C(Predicted)
• 密度：
  1.379±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2-((4-methylphenyl)sulfonamido)-3-(4-(tosyloxy)phenyl)propanoic acid 在 氢氧化钾 、 水 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 7.0h， 生成 (S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid
  参考文献：
  名称：

  WO2008/22462

  摘要：

  公开号：
• 作为产物：
  描述：

  L-酪氨酸 、 对甲苯磺酰氯 以 四氢呋喃 、 水 为溶剂， 生成 (S)-2-((4-methylphenyl)sulfonamido)-3-(4-(tosyloxy)phenyl)propanoic acid
  参考文献：
  名称：

  Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N–H/C(sp³)–H Coupling

  摘要：

  An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp(3))-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp(3))-H bonds were aminated, and various functional groups were tolerated.

  DOI：

  10.1021/acs.joc.9b01154

文献信息

• Stereoselective synthesis and applications of nitrogen substituted donor–acceptor cyclopropanes (N-DACs) in the divergent synthesis of azacycles
  作者：Santosh J. Gharpure、U. Vijayasree、S. Raja Bhushan Reddy

  DOI：10.1039/c2ob06591f

  日期：——

  A new, highly stereoselective intramolecular cyclopropanation of vinylogous carbamates with carbenes in the presence of Cu(acac)2 as the catalyst has been developed for the construction of cyclopropapyrrolidinones. The ‘syn’ isomer of N-DAC can be converted to the ‘anti’ isomer by simple silica gel treatment. Regioselective cleavage of each of the cyclopropane bonds of these two acceptor substituted N-DACs led to a diverse array of azacycles.

  开发了一种新型的高立体选择性分子内烯丙基氨基甲酸酯与卡宾的环丙烷化反应，以Cu(acac)2为催化剂，用于构建环丙烷吡咯烷酮。通过简单的硅胶处理，可将N-DAC的顺式异构体转化为反式异构体。这两种受体取代的N-DAC的环丙烷键的区域选择性断裂，产生了一系列多样性的氮杂环化合物。
• Metal-Free N-H/C-H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α-Amino Acids
  作者：Kyalo Stephen Kanyiva、Masashi Horiuchi、Takanori Shibata

  DOI：10.1002/ejoc.201800012

  日期：2018.2.28

  The synthesis of dihydroquinoxalinones via intramolecular N–H/C–H coupling using hypervalent iodine from inexpensive and readily available aniline and amino acid derivatives was developed. Many functional groups were tolerated to give various dihydroquinoxalinones in moderate to excellent yields. The chirality of the amino acid was transferred to the desired target compound without loss of enantiomeric

  已开发了通过分子内N–H / C–H偶联使用高价碘从廉价且容易获得的苯胺和氨基酸衍生物合成二氢喹喔啉酮的方法。容许许多官能团以中等至优异的产率产生各种二氢喹喔啉酮。氨基酸的手性被转移到所需的目标化合物上，而对映体过量没有损失。
• The Overman rearrangement in carbohydrate chemistry: stereoselective synthesis of functionalized 3-amino-3,6-dihydro-2H-pyrans and incorporation in peptide derivatives
  作者：Ana Montero、Enrique Mann、Bernardo Herradón

  DOI：10.1016/j.tetlet.2004.11.109

  日期：2005.1

  A stereocontrolled synthesis of an unsaturated sugar bearing two amino groups (one of them masked as an azide), using an Overman rearrangement as key step, is described. This scaffold is used to prepare two peptides having aromatic fragments, which have shown activity as calpain inhibitors.

  描述了使用Overman重排作为关键步骤的立体控制合成的不饱和糖，该不饱和糖带有两个氨基（其中一个被掩盖为叠氮基）。该支架用于制备具有芳族片段的两种肽，它们已显示出作为钙蛋白酶抑制剂的活性。
• PARA-QUINOL DERIVATIVES AND METHODS OF STEREO SELECTIVELY SYNTHESIZING AND USING SAME
  申请人：Plourde Guy L.

  公开号：US20090318548A1

  公开（公告）日：2009-12-24

  This application relates to para-quinol derivatives, such as analogues of manumycins, aranorosins and gymnastatins. This application also relates to methods of synthesizing and using the para-quinol derivatives. In one embodiment of the invention a compound having the chemical structure (I) is provided wherein X 1 and X 2 are carbon atoms either joined by double bond or joined by a single bond and comprising constituents of an epoxide ring or a hydroxyethylene moiety; X 3 and X 4 are carbon atoms either joined by double bond or joined by a single bond and comprising constituents of an epoxide ring; R 1 is selected from the group consisting of branched alkyl chains, unbranched alkyl chains, cycloalkyl groups, aromatic groups, alcohols, ethers, amines, and substituted or unsubstituted ureas, esters, aldehydes and carboxylic acids; and R 2 is selected from the group consisting of H, OH and NHR 3 wherein R 3 is a nitrogen protecting group. In a particular embodiment of the invention R 1 is a polyunsaturated carbon chain as found in biologically active manumycins. The applicant's synthetic method may involve diasteroselective formation of a spirolactone in an oxidative spiroannulation process using tyrosine or a tyrosine derivative having a chiral centre as a starting material.

  本申请涉及对位喹啉衍生物，例如曼纽霉素、阿拉诺罗辛和体操霉素的类似物。本申请还涉及合成和使用对位喹啉衍生物的方法。在发明的一个实施例中，提供了具有化学结构（I）的化合物，其中X1和X2是由双键连接或单键连接的碳原子，并包括环氧环或羟基乙烯基的组分；X3和X4是由双键连接或单键连接的碳原子，并包括环氧环的组分；R1选自支链烷基链，直链烷基链，环烷基团，芳香族团，醇，醚，胺和取代或未取代的脲、酯、醛和羧酸；R2选自H，OH和NHR3，其中R3是氮保护基。在发明的一个特定实施例中，R1是生物活性曼纽霉素中发现的多不饱和碳链。申请人的合成方法可能涉及使用酪氨酸或手性中心的酪氨酸衍生物作为起始材料，在氧化螺环化过程中二面体选择性地形成螺内酯。
• Construction of Thioamide Peptides from Chiral Amino Acids
  作者：Yanyan Liao、Shunmin Zhang、Xuefeng Jiang

  DOI：10.1002/anie.202303625

  日期：2023.6.26

  Straightforward linking of natural α-amino acids in the presence of thiolphosphonate and trichlorosilane was established to construct various thioamide-containing peptides. The carbonyl group is replaced with a thiono group by sequential activation, and the chirality of the amino acid component is maintained in the products.

  建立了在硫代膦酸酯和三氯硅烷存在下天然α-氨基酸的直接连接，以构建各种含硫代酰胺的肽。通过连续活化，羰基被硫代基取代，产物中保持了氨基酸成分的手性。