(2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidine-4-carboxylic acid | 158446-52-7

• 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: (2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidine-4-carboxylic acid
• 英文别名: (2R,4R)-3-(tert-Butoxycarbonyl)-2-phenyl-4-thiazolidincarbonsaeure；(2R,4R)-3-[(2-methylpropan-2-yl)oxycarbonyl]-2-phenyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 158446-52-7
• 化学式: C₁₅H₁₉NO₄S
• 分子量: 309.386
• InChiKey: QTGJLLUGEPDNFX-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidine-4-carboxylic acid 在 吡啶 、 氨 、 sodium 、 二异丁基氢化铝 、 二氯磷酸苯酯 、 N,N-二甲基甲酰胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 25.5h， 生成 1,1-Dimethylethyl -(3,6,7,8,9,10-hexahydro-10-oxo-2H-thiecin-3-yl)carbamate
  参考文献：
  名称：

  Novel Enantioselective Syntheses of (+)-Biotin

  摘要：

  Two conceptually attractive enantioselective syntheses of(+)-biotin from L-cysteine are reported based upon an intramolecular 1,3-dipolar cycloaddition of a carbamoyl azide. The first approach (12 steps) involves the following as key-steps: (i) the macrothiolactonization of acid 10b to Z-olefin 14, (ii) the thermolysis of the ene carbamoyl azide 15 in water with direct formation of a mixture of the benzylated derivatives of(+)-biotin 16a and 17a. The second approach (14 steps) involves the following: (i) elimination of bromide 29 to the endocyclic thioenol ether 30, (ii) thermolysis of the ene carbamoyl azide 30 to the exocyclic thioenol ethers 31a and 31b. Both the synthesis of 29 and the final transformation of 31a and 31b into (+)-biotin are based upon literature precedents.

  DOI：

  10.1021/jo00107a009
• 作为产物：
  描述：

  苯甲醛 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 16.0h， 生成 (2R,4R)-3-(tert-butoxycarbonyl)-2-phenylthiazolidine-4-carboxylic acid
  参考文献：
  名称：

  Synthesis, characterization and antibacterial activities of N-tert-butoxycarbonyl-thiazolidine carboxylic acid

  摘要：

  动力学选择性分辨机制是通过形成N-Boc-TCAs的分子内氢键进行亲核取代，根据Curtin-Hammett原理提出了定性解释。

  DOI：

  10.1039/c4ra15284k

文献信息

• Absolute Configuration and Total Synthesis of (+)-Curacin A, an Antiproliferative Agent from the Cyanobacterium <i>Lyngbya majuscula</i>
  作者：James D. White、Tae-Seong Kim、Mitch Nambu

  DOI：10.1021/ja9629874

  日期：1997.1.1

  The absolute configuration of curacin A was determined as (2R,13R,19R,21S)-1 by comparison of degradation products 2 and 3 with the same materials prepared by asymmetric synthesis. The total synthesis of 1 was completed from (1R,2S)-2-methylcyclopropanecarboxylic acid (8) and the amino alcohol derivative 46. The latter was prepared from 4-pentynal (14) and the Garner aldehyde (43). Asymmetric allylation

  通过将降解产物 2 和 3 与通过不对称合成制备的相同材料进行比较，确定 curacin A 的绝对构型为 (2R,13R,19R,21S)-1。1的全合成由(1R,2S)-2-甲基环丙烷羧酸(8)和氨基醇衍生物46完成。后者由4-戊醛(14)和加纳醛(43)制备。14 的不对称烯丙基化，然后衍生的醇 16 的甲基化得到 17，将其进行锆化-碘化得到 18。后者与硼酸乙烯酯 21 偶联，后者由乙酸 4-戊炔酯 (20) 制备，在Pd(0)和所得三烯醇22被转化为碘化鏻24。来自24的叶立德与43的Wittig反应提供四烯44，其在甲醇分解时产生45。
• Synthesis of a Series of Hexitol and Aminodeoxyhexitol Mononitrate Derivatives Containing a Sulfur Group and Pharmacological Evaluation on Isolated Rat Aortas
  作者：Jean Pierre Nallet、Anne Lise Mégard、Christian Arnaud、Denis Bouchu、Pierre Lantéri、Marie-Luce Béa、Vincent Richard、Alain Berdeaux

  DOI：10.1002/(sici)1099-0690(199805)1998:5<933::aid-ejoc933>3.0.co;2-j

  日期：1998.5

  possible influence on tolerance phenomenon, it was important to check the vasorelaxing effects of our compounds compared to those of commercial organic nitrates of similar structures such as isosorbide mononitrate or isosorbide dinitrate. All the compounds were tested on isolated rat aortas; some of these products exhibited an interesting activity.

  作为我们研究用于治疗心绞痛的新型有机硝酸盐的一部分，我们研究了一系列含有硫基团的己糖醇和氨基脱氧己糖醇单硝酸酯衍生物。由于巯基的组织储存的消耗似乎在这种现象的发展中起重要作用，因此在硝酸盐衍生物中添加硫基团可以防止长期治疗期间硝酸盐耐受性的发展。在研究作用持续时间和对耐受现象的可能影响之前，重要的是检查我们的化合物与类似结构的商业有机硝酸盐（如单硝酸异山梨酯或硝酸异山梨酯）的血管舒张作用相比。所有化合物均在离体的大鼠主动脉上进行测试；
• LIPOPROTEINS, LIPOPEPTIDES AND ANALOGS, AND METHODS FOR MAKING AND USING THEM
  申请人：Gerwick William

  公开号：US20100266675A1

  公开（公告）日：2010-10-21

  The invention provides novel compositions—lipopeptides and analogs, including somocystinamide A, and somocystinamide A variants and analogs, and pharmaceutical compositions, liposomes and nanoparticles comprising them, and methods of making and using them. In one embodiment, these lipopeptides and analogs are used to induce apoptosis in a cell, which can be a normal cell, a dysfunctional cell and/or a cancer (tumor) cell. In alternative embodiments, the compositions of the invention, including the lipopeptides and analogs of the invention, and the pharmaceutical compositions comprising them, are used to treat or ameliorate (including slowing the progression of) normal, dysfunctional (e.g., abnormally proliferating) and/or tumor associated blood vessels, including endothelial and/or capillary cell growth; including neovasculature related to (within, providing a blood supply to) a tumor.

  本发明提供了新型组合物——脂肽和类似物，包括somocystinamide A和somocystinamide A的变体和类似物，以及包含它们的药物组合物、脂质体和纳米粒子，以及制备和使用它们的方法。在一种实施例中，这些脂肽和类似物被用来诱导细胞凋亡，这可以是正常细胞、功能失调的细胞和/或癌细胞。在另一种实施例中，本发明的组合物，包括本发明的脂肽和类似物以及包含它们的药物组合物，被用于治疗或改善（包括减缓进展）正常、功能失调（例如异常增殖）和/或与肿瘤相关的血管，包括内皮和/或毛细血管细胞生长；包括与肿瘤相关的新生血管（在肿瘤内部提供血液供应）。
• Rearrangement of thiazolidine derivatives – a synthesis of a chiral fused oxathiane–γ-lactam bicyclic system
  作者：Karolina Kamińska、Dominika Iwan、Jakub Trojnar、Marek Daszkiewicz、Joanna E. Rode、Jacek Wojaczyński、Elżbieta Wojaczyńska

  DOI：10.1039/d3ob01454a

  日期：——

  Reaction of L-cysteine with carbonyl compounds leads to thiazolidine derivatives which undergo a stereoselective conversion to two types of chiral bicyclic products bearing two or three stereogenic centers, including the first fused oxathiane–γ-lactam system.

  L-半胱氨酸与羰基化合物的反应产生噻唑烷衍生物，其立体选择性转化为两种类型的带有两个或三个立体中心的手性双环产物，包括第一个稠合氧噻烷-γ-内酰胺系统。
• Heterocyclische Verbindungen aus Zuckern, XV: Zur Konfiguration chiraler C-2-substituierter 4-Thiazolidincarbons�uren. Chiralit�tstransfer auf C-3 in 3,4-Dihydro-1H-pyrrolo[1,2-c]thiazolen
  作者：Z. Gy�rgyde�k、L. Szil�gyi、J. Kajt�r、G. Argay、A. K�lm�n

  DOI：10.1007/bf00818164

  日期：1994.2

  5-Substituted 3,4-dihydro-pyrrolo[1,2-c]thiazole-6,7-dicarboxylic acid esters 3 are obtained from 2-substituted-3-acyl-1,3-thiazolidine-4-carboxylic acids, 1 in [3 + 2]-cycloaddition reactions via mesoionic oxazolone (''munchnone'') intermediates. The chirality at C-4 of the starting carboxylic acids 1 is eliminated in the products 3, and the chirality at C-3 (C-2 in the starting carboxylic acids 1) can thus be determined through chiroptical measurements. Several representatives of the ring system 3 have been characterised through H-1- and CD-spectra and the molecular structure of (3S)-3da has been determined by X-ray crystallography.