methyl (S)-2-(tert-butoxycarbonylamino)-6-hydroxyhexanoate | 81505-49-9

• 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: methyl (S)-2-(tert-butoxycarbonylamino)-6-hydroxyhexanoate
• 英文别名: (S)-2-tert-butoxycarbonylamino-6-hydroxy-hexanoic acid methyl ester；methyl (2S)-6-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 81505-49-9
• 化学式: C₁₂H₂₃NO₅
• 分子量: 261.318
• InChiKey: RROCSCBJUBRRQV-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-(tert-butoxycarbonylamino)-6-hydroxyhexanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 (S)-2-amino-6-hydroxy-hexanoic acid methyl ester
  参考文献：
  名称：

  (S)-(-)-1-[(9-FLUORENYLMETHOXYCARBONYL)AMINO-5-CARBOXYPENTYL]-3-羟基吡啶三氟乙酸盐的合成

  摘要：

  (X)-(-)1-(amino-5-carboxypentyl]-3-hydroxypyridinium salt 1 的衍生物存在于骨胶原中，在维持该组织的完整性方面起着重要作用。'.' 外消旋 ( k)-l 从叔丁基-(2-叔丁氧基羰基) 氨基乙酸酯开始已有报道。' 我们在此介绍了一种重要的手性结构单元的制备，0)-(-)-Fmoc 衍生物 1（化合物2)，需要通过固相技术合成包含胶原蛋白的肽。因此，由Na-叔-Boc-赖氨酸制备的(S)-(-)-甲基2-[(叔丁氧基羰基)氨基]-6-羟基戊酸酯(3)？用三氟乙酸在二氯甲烷中水解，得到 (S)-胺 (4)，无需纯化，用氯甲酸 9-芴基甲酯 5 处理，以 65% 的收率得到 (S)-(-)-甲基 2-[(9-芴基甲氧基羰基) 氨基]-6 羟基戊酸酯 (5)。使用碘、三苯基膦和咪唑将 (9 -5 中的羟基官能团转化为相应的碘化物 (S)-(+)-6，产率为

  DOI：

  10.1080/00304940009355922
• 作为产物：
  描述：

  (E)-(S)-2-tert-Butoxycarbonylamino-6-hydroxy-hex-4-enoic acid methyl ester 在 platinum(IV) oxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 以97%的产率得到methyl (S)-2-(tert-butoxycarbonylamino)-6-hydroxyhexanoate
  参考文献：
  名称：

  A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor

  摘要：

  A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H-2-receptor, has been developed in 10 steps and in 31% overall yield from L-aspartic acid. The key steps involved a two-carbon homologation of an L-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.165

文献信息

• CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS
  申请人：POLYPHOR AG

  公开号：US20150051183A1

  公开（公告）日：2015-02-19

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义的大环环系统由三个不同的分子部分组成：模板A、构象调节剂B和桥C。由这种环系统I描述的大环可通过并行合成或溶液中或固相上的组合化学轻松制造。它们被设计用于与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，酶的抑制活性或抗菌活性。特别是，这些大环显示对亚型1的内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶卡特普辛S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃素3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• Catalytic Asymmetric Hydrogenation of Dehydroamino Acid Esters with Biscarbamate Protection and Its Application to the Synthesis of xCT Inhibitors
  作者：Yoko Yasuno、Iho Mizutani、Yuki Sueuchi、Yuuka Wakabayashi、Nozomi Yasuo、Keiko Shimamoto、Tetsuro Shinada

  DOI：10.1002/chem.201900289

  日期：2019.4.5

  Catalytic asymmetric hydrogenation of dehydroamino acid esters with biscarbamate protection was examined for the first time to prepare optically active amino acids. The new method was successfully applied to the synthesis of new cystine–glutamate exchanger inhibitors.

  首次检查了具有双氨基甲酸酯保护作用的脱氢氨基酸酯的催化不对称氢化反应，以制备旋光性氨基酸。该新方法已成功应用于新的胱氨酸-谷氨酸交换抑制剂的合成。
• Combined application of organozinc chemistry and one-pot hydroboration–Suzuki coupling to the synthesis of amino acids
  作者：Arantxa Rodríguez、David D. Miller、Richard F. W. Jackson

  DOI：10.1039/b300536d

  日期：2003.3.13

  Hydroboration using 9-BBN-H of the protected enantiomerically pure but-3-enylglycine derivative 11, prepared by copper-catalysed allylation of the serine-derived organozinc reagent 1, followed by Suzuki coupling of the derived borane with a variety of aromatic halides, 2-bromopyridine and 2-bromopropene gives the protected amino acids 14a–l and 15. This method augments our previous methods for the synthesis of phenylalanine homologues.

  使用9-BBN-H对保护的手性纯的丁-3-烯基甘氨酸衍生物11进行氢硼化，该衍生物是通过铜催化的烯丙基化反应得到的，反应中使用了源自丝氨酸的有机锌试剂1，之后与多种芳香卤化物（如2-溴吡啶和2-溴丙烯）进行铃木偶联反应，得到保护的氨基酸14a-l和15。这种方法增强了我们之前合成苯丙氨酸同源物的策略。
• [EN] CONFORMATIONALLY CONSTRAINED, FULLY SYNTHETIC MACROCYCLIC COMPOUNDS<br/>[FR] COMPOSÉS MACROCYCLIQUES ENTIÈREMENT SYNTHÉTIQUES ET À CONFORMATION CONTRAINTE
  申请人：POLYPHOR AG

  公开号：WO2013139697A1

  公开（公告）日：2013-09-26

  The conformationally restricted, spatially defined macrocyclic ring system of formula (I) is constituted by three distinct molecular parts: Template A, conformation Modulator B and Bridge C. Macrocycles described by this ring system I are readily manufactured by parallel synthesis or combinatorial chemistry in solution or on solid phase. They are designed to interact with a variety of specific biological target classes, examples being agonistic or antagonistic activity on G-protein coupled receptors (GPCRs), inhibitory activity on enzymes or antimicrobial activity. In particular, these macrocycles show inhibitory activity on endothelin converting enzyme of subtype 1 (ECE-1 ) and/or the cysteine protease cathepsin S (CatS), and/or act as antagonists of the oxytocin (OT) receptor, thyrotropin-releasing hormone (TRH) receptor and/or leukotriene B4 (LTB4) receptor, and/or as agonists of the bombesin 3 (BB3) receptor, and/or show antimicrobial activity against at least one bacterial strain. Thus they are showing great potential as medicaments for a variety of diseases.

  公式（I）的构象受限、空间定义明确的大环环形系统由三个不同的分子部分构成：模板A、构象调制剂B和桥梁C。由该环系统I描述的大环可通过溶液中的并行合成或组合化学，或者在固相上制造。它们被设计用来与各种特定生物靶标类相互作用，例如在G蛋白偶联受体（GPCR）上的激动或拮抗活性，对酶的抑制活性或抗菌活性。特别是，这些大环显示对第1亚型内皮素转化酶（ECE-1）和/或半胱氨酸蛋白酶S（CatS）的抑制活性，和/或作为催产素（OT）受体、促甲状腺释放激素（TRH）受体和/或白三烯B4（LTB4）受体的拮抗剂，和/或作为瘤胃肽3（BB3）受体的激动剂，和/或对至少一种细菌菌株显示抗菌活性。因此，它们显示出作为各种疾病药物的巨大潜力。
• Cyclic derivatives as modulators of chemokine receptor activity
  申请人：Cherney J. Robert

  公开号：US20070032541A1

  公开（公告）日：2007-02-08

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of rheumatoid arthritis, multiple sclerosis, atherosclerosis and asthma, processes for preparing and intermediates thereof.

  本申请描述了 MCP-1 的调节剂，其化学式为 (I) 或其药学上可接受的盐形式，可用于预防类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘，以及其制备过程和中间体。