N-(tert-butoxycarbonyl)-O-(p-toluenesulfonyl)-DL-serine methyl ester | 69961-11-1

• 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-(tert-butoxycarbonyl)-O-(p-toluenesulfonyl)-DL-serine methyl ester
• 英文别名: 2-tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-propionic acid methyl ester；N-tert-butoxycarbonyl-O-p-toluenesulfonylserin methyl ester；methyl 3-(p-toluenesulfonyloxy)-2-(S)-(t-butoxycarbonylamino)propionate；methyl 3-(4-methylphenyl)sulfonyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 69961-11-1
• 化学式: C₁₆H₂₃NO₇S
• 分子量: 373.427
• InChiKey: VVBLIPVUGGNLGW-UHFFFAOYSA-N

物化性质

• 沸点：
  520.0±50.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-O-(p-toluenesulfonyl)-DL-serine methyl ester 在 二乙胺 作用下， 以 乙醚 、 乙酸乙酯 为溶剂， 生成 2-叔丁氧羰基氨基丙烯酸甲酯
  参考文献：
  名称：

  Serine derived NK1 antagonists 1: The effect of modifications to the serine substituents

  摘要：

  A series of novel serine derived NK, antagonists is described. The effect of variations in the N-benzyl, O-benzyl and serine groups are used to define the elements which are necessary for binding. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00320-5
• 作为产物：
  描述：

  BOC-DL-丝氨酸 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 N-(tert-butoxycarbonyl)-O-(p-toluenesulfonyl)-DL-serine methyl ester
  参考文献：
  名称：

  Improved synthetic routes to the selenocysteine derivatives useful for Boc-based peptide synthesis with benzylic protection on the selenium atom

  摘要：

  Selenocysteine (Sec) derivatives, i.e., Boc-Sec(MBn)-OH (1) and Boc-Sec(MPM)-OH (2), which are useful for chemical synthesis of selenopeptides, were obtained from L-serine in five steps with total yields of 73% and 74%, respectively. The enantiomeric excesses were confirmed to be >99% e.e. by optical resolution using a chiral column on HPLC. On the other hand, for the case of a Fmoc-protected Sec derivative, i.e., Fmoc-Sec( MPM)-OH, similar reactions resulted in low yields and partial racemization taking place.

  DOI：

  10.3998/ark.5550190.p009.803

文献信息

• Carbocyclic HIV protease inhibitors
  申请人：Hoffmann-La Roche Inc.

  公开号：US06632826B1

  公开（公告）日：2003-10-14

  The present invention is concerned with novel HIV protease Inhibitors of formula I as individual isomers, racemates, non-racemic mixtures or mixtures of diastereoisomers; wherein n, R1 and R4 are as described herein. The compounds of formula I are peptide mimetics which act as inhibitors of the HIV aspartyl protease, an essential enzyme in the replicative life cycle of HIV.

  本发明涉及一种新型HIV蛋白酶抑制剂，其化学式为I型，可以是单体异构体、外消旋体、非外消旋混合物或二对映异构物的混合物；其中n、R1和R4如本文所述。化合物I的化学式是肽类模拟物，作为HIV天冬氨酸蛋白酶的抑制剂，这是HIV复制生命周期中不可或缺的酶。
• Total Synthesis of Cribrostatin IV:  Fine-Tuning the Character of an Amide Bond by Remote Control
  作者：Collin Chan、Richard Heid、Shengping Zheng、Jinsong Guo、Bishan Zhou、Takeshi Furuuchi、Samuel J. Danishefsky

  DOI：10.1021/ja050203t

  日期：2005.4.1

  We report the enantioselective total synthesis of cribrostatin IV (1). Key features of this synthesis involve the convergent coupling of two highly functionalized homochiral components followed by a "lynchpin" Mannich cyclization to establish the pentacyclic core (cf. 19 --> 20).

  我们报告了 cribrostatin IV 的对映选择性全合成 (1)。这种合成的关键特征包括两个高度功能化的同手性成分的会聚耦合，然后是“关键”曼尼希环化以建立五环核心（参见 19 --> 20）。
• Pentacyclic Alkaloid Compounds and Methods of Use Thereof
  申请人：Danishefsky Samuel J.

  公开号：US20090325971A1

  公开（公告）日：2009-12-31

  The present invention relates to Pentacyclic Alkaloid Compounds, compositions comprising an effective amount of a Pentacyclic Alkaloid Compound and methods for treating or preventing cancer, a bacterial infection, a fungal infection, or a yeast infection, comprising administering to a subject in need thereof an effective amount of a Pentacyclic Alkaloid Compound. The present invention also relates to compounds and methods that are useful for making Cribrostatin IV.

  本发明涉及五环生物碱化合物、包含有效量五环生物碱化合物的组合物以及治疗或预防癌症、细菌感染、真菌感染或酵母菌感染的方法，包括向需要的受试者施用有效量的五环生物碱化合物。本发明还涉及有用于制备Cribrostatin IV的化合物和方法。
• Metallkomplexe mit biologisch wichtigen Liganden, LXXXIX. Oxidative Addition von elektrophilen α‐Aminosäurederivaten an Platin(II)‐ und Cobalt(I)‐Komplexe: α‐Übergangsmetallierte Aminosäuren
  作者：Bernd Kayser、Heirnrich Nöth、Martin Schmidt、Wolfgang Steglich、Wolfgang Beck

  DOI：10.1002/cber.19961291231

  日期：1996.12

  Metal Complexes of Biologically Important Ligands, LXXXIX1 . — Oxidative Addition of Electrophilic Derivatives of α-Amino Acids to Platinum(II) and Cobalt(I) Complexes: α-Transition-Metallated Amino Acids2

  生物重要配体的金属配合物，LXXXIX 1 。—α-氨基酸亲电衍生物向铂（II）和钴（I）配合物的氧化加成：α-过渡金属化氨基酸2
• Utilisation des organocuprates a la synthese d'aminoacides
  作者：A. Bernardini、A. El Hallaoui、R. Jacquier、Ch. Pigière、Ph. Viallefont、J. Bajgrowicz

  DOI：10.1016/s0040-4039(00)94517-9

  日期：1983.1