(S)-n-boc-3-氨基-4-羟基丁酸 | 83345-44-2

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-n-boc-3-氨基-4-羟基丁酸
• 中文别名: (3S)-3-[[叔丁氧羰基]氨基]-4-羟基丁酸
• 英文名称: (S)-3-((tert-Butoxycarbonyl)amino)-4-hydroxybutanoic acid
• 英文别名: (3S)-4-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid
• CAS: 83345-44-2
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: PRSIONPHFVWSKD-LURJTMIESA-N

物化性质

• 沸点：
  416.9±40.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  (S)-n-boc-3-氨基-4-羟基丁酸 在 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 methyl (S)-3-((tert-butoxycarbonyl)amino)-4-(5-chloro-1H-indole-2-carboxamido)butanoate
  参考文献：
  名称：

  Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

  摘要：

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.132
• 作为产物：
  描述：

  benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 生成 (S)-n-boc-3-氨基-4-羟基丁酸
  参考文献：
  名称：

  Design, synthesis and SAR of novel ethylenediamine and phenylenediamine derivatives as factor Xa inhibitors

  摘要：

  We previously reported on a series of cyclohexanediamine derivatives as highly potent factor Xa inhibitors. Herein, we describe the modification of the spacer moiety to discover an alternative scaffold. Ethylenediamine derivatives possessing a substituent at the C1 position in S configuration and phenylenediamine derivatives possessing a substituent at the C5 position demonstrated moderate to strong anti-fXa activity. Further SAR studies led to the identification of compound 30h which showed both good in vitro activity (fXa IC50 = 2.2 nM, PTCT2 = 3.9 mu M) and in vivo antithrombotic efficacy. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.132

文献信息

• [EN] BETA-SUBSTITUTED BETA-AMINO ACIDS AND ANALOGS AS CHEMOTHERAPEUTIC AGENTS AND USES THEREOF<br/>[FR] ACIDES BÊTA-AMINÉS SUBSTITUÉS EN BÊTA ET ANALOGUES À UTILISER EN TANT QU'AGENTS DE CHIMIOTHÉRAPIE ET LEURS UTILISATIONS
  申请人：QUADRIGA BIOSCIENCES INC

  公开号：WO2017024009A1

  公开（公告）日：2017-02-09

  β-Substituted β-amino acids, β-substituted β-amino acid derivatives, and β-substituted β-amino acid analogs and (bio)isosteres and their use as chemotherapeutic agents are disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres are selective LAT1/4F2hc substrates and exhibit rapid uptake and retention in tumors expressing the LAT1/4F2hc transporter. Methods of synthesizing the β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and methods of using the compounds for treating cancer are also disclosed. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs exhibit selective uptake in tumor cells expressing the LAT1/4F2hc transporter and accumulate in cancerous cells when administered to a subject in vivo. The β-substituted β-amino acid derivatives and β-substituted β-amino acid analogs and (bio)isosteres exhibit cytotoxicity toward several tumor types.

  β-取代β-氨基酸，β-取代β-氨基酸衍生物，β-取代β-氨基酸类似物和（生物）同位素以及它们作为化疗药物的用途被披露。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素是选择性LAT1/4F2hc底物，并在表达LAT1/4F2hc转运蛋白的肿瘤中表现出快速摄取和保留。还披露了合成β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物的方法以及使用这些化合物治疗癌症的方法。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物在表达LAT1/4F2hc转运蛋白的肿瘤细胞中表现出选择性摄取，并在体内给予受试者后在癌细胞中积累。β-取代β-氨基酸衍生物和β-取代β-氨基酸类似物和（生物）同位素对几种肿瘤类型表现出细胞毒性。
• Cathepsin cysteine protease inhibitors
  申请人：Gauthier Yves Jacques

  公开号：US20060111440A1

  公开（公告）日：2006-05-25

  This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.

  这项发明涉及一类新型化合物，它们是半胱氨酸蛋白酶抑制剂，包括但不限于对卡特普辛K、L、S和B的抑制剂。这些化合物可用于治疗需要抑制骨吸收的疾病，如骨质疏松症。
• [EN] CATHEPSIN CYSTEINE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DES PROTEASES A CYSTEINE DU TYPE CATHEPSINE
  申请人：MERCK FROSST CANADA INC

  公开号：WO2005056529A1

  公开（公告）日：2005-06-23

  This invention relates to a novel class of compounds which are cysteine protease inhibitors, including but not limited to, inhibitors of cathepsins K, L, S and B. These compounds are useful for treating diseases in which inhibition of bone resorption is indicated, such as osteoporosis.

  这项发明涉及一类新型化合物，它们是半胱氨酸蛋白酶抑制剂，包括但不限于对卡特普辛K、L、S和B的抑制剂。这些化合物对于治疗需要抑制骨吸收的疾病，如骨质疏松症，非常有用。
• A New Entry to Polyfunctionalized4,5-<i>trans</i>Disubstituted Oxazolidin-2-ones from<scp>l</scp>-Aspartic Acid
  作者：Claudia Tomasini、Gianluigi Luppi

  DOI：10.1055/s-2003-38733

  日期：——

  A straightforward synthesis of enantiomerically pure (4R,5S)-5-oxazolidinecarboxylic acid, 2-oxo-4-[(t-butyldimethyl­silyloxy)methyl]-, benzyl ester and of (4S,5S)-4-oxazolidinecarboxylic acid, 2-oxo-5-[(t-butyldimethylsilyloxy)methyl]-, benzyl ester was envisaged starting from readily available l-aspartic acid. The key step is the diastereoselective addition of iodine with the introduction of a new stereogenic centre.

  一种简单的合成方法被设想用于手性纯（4R,5S）-5-氧杂植物酸、2-氧-4-[(t-丁基二甲基硅氧基)甲基]-苄酯和（4S,5S）-4-氧杂植物酸、2-氧-5-[(t-丁基二甲基硅氧基)甲基]-苄酯，起始材料为容易获得的L-天冬氨酸。关键步骤是碘的二源选择性加成，伴随引入一个新的立体中心。
• Syntheses of four unusual amino acids, constituents of cyclomarin A
  作者：Hideyuki Sugiyama、Takayuki Shioiri、Fumiaki Yokokawa

  DOI：10.1016/s0040-4039(02)00607-x

  日期：2002.5

  amino acids, constituents of cyclomarin A, are described. The protected N-methylhydroxyleucine 2 was synthesized using Evans’ asymmetric azide-transfer reaction. The unusual amino acid 3 was prepared via diastereoselective methylation of the l-aspartic acid derived lactone 13. The stereoselective formation of threo-β-methoxyphenylalanine 4 was performed via aldol reaction using Schöllkopf's chiral glycine

  描述了四种非常规氨基酸的立体选择性合成，它们是环marinA的组成部分。使用Evans的不对称叠氮化物转移反应合成了被保护的N-甲基羟基亮氨酸2。通过L-天冬氨酸衍生的内酯13的非对映选择性甲基化制备了不寻常的氨基酸3。使用Schöllkopf's手性甘氨酸烯醇酸酯通过醛醇缩合反应进行苏-β-甲氧基苯基丙氨酸4的立体选择性形成。通过AQN配体促进的Sharpless区域逆向不对称氨基羟基化方案实现了N-反向的戊烯基色氨酸5的合成。