L-丝氨酸苄酯苯磺酸盐 | 3695-68-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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
• 中文名称: L-丝氨酸苄酯苯磺酸盐
• 英文名称: L-serine benzyl ester benzenesulfonate
• 英文别名: L-serine benzyl ester benzenesulfonate salt；L-Serin-benzylester; Benzolsulfonat；L-Serine benzyl ester benzenesulfonate (salt)；benzenesulfonic acid;benzyl (2S)-2-amino-3-hydroxypropanoate
• CAS: 3695-68-9
• 化学式: C₆H₆O₃S*C₁₀H₁₃NO₃
• 分子量: 353.396
• InChiKey: AJKFQGHWMCPNTI-FVGYRXGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

安全信息

• WGK Germany：
  3
• 海关编码：
  2922509090
• 储存条件：
  储存条件：密封、干燥，并在惰性气体环境中保持在2-8°C。

制备方法与用途

L-丝氨酸苄基酯苯磺酸（盐）是一种丝氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  L-丝氨酸苄酯苯磺酸盐 在 bis(tri-o-tolylphosphine)palladium trichloride 吡啶 、 sodium hydroxide 、 锌铜偶 、 sodium iodide 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 50.5h， 生成 N-叔丁氧羰基-L-苯丙氨酸苄酯
  参考文献：
  名称：

  Preparation of enantiomerically pure protected 4-oxo .alpha.-amino acids and 3-aryl .alpha.-amino acids from serine

  摘要：

  The organozinc reagent 13, prepared from the protected beta-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-alpha-amino acids 17 in 39-90% yield (13 examples). Zinc reagent 13 can also be coupled with aryl iodides in the presence of bis(tri-o-tolylphosphine)palladium dichloride to give enantiomerically pure protected phenylalanine analogues 26, 29, and 30 in 10-67% yield (11 examples). The reaction tolerates the presence of a variety of functional groups in the acid chloride and the aryl iodide and provides derivatives which can be easily deprotected, at either the carboxyl or amino terminus, to give intermediates suitable for peptide synthesis.

  DOI：

  10.1021/jo00038a030

文献信息

• [EN] TREPROSTINIL PRODRUGS<br/>[FR] PROMÉDICAMENTS DE TRÉPROSTINIL
  申请人：UNITED THERAPEUTICS CORP

  公开号：WO2018058124A1

  公开（公告）日：2018-03-29

  Provided are novel prodrugs of treprostinil, as well as methods of making and methods of using these prodrugs.

  提供了特瑞普罗斯汀的新型前药，以及制备这些前药和使用这些前药的方法。
• [EN] CONTINUOUS FLOW PROCESS FOR THE PRODUCTION OF DIAZO ESTERS<br/>[FR] PROCÉDÉ À ÉCOULEMENT CONTINU POUR LA PRODUCTION D'ESTERS DIAZOÏQUES
  申请人：SIGMA ALDRICH CO LLC

  公开号：WO2012128985A1

  公开（公告）日：2012-09-27

  Processes for producing diazo ester derivatives in a single phase system in a continuous flow reactor.

  在连续流反应器中单相系统中生产重氮酯衍生物的工艺。
• 4-Cyanobenzenesulfonamides: Amine Synthesis and Protecting Strategy To Compliment the Nosyl Group
  作者：Michael A. Schmidt、Ryjul W. Stokes、Merrill L. Davies、Frederick Roberts

  DOI：10.1021/acs.joc.7b00608

  日期：2017.5.5

  amine protecting/activating group within a broader context of amine synthesis. The crystalline sulfonamides could be further elaborated by alkylation and arylation similarly to nitrobenzenesulfonamides. The sulfonamides could withstand conditions that functionalize nitroarenes, such as reductions and vicarious nucleophilic substitution reactions.

  发现仲胺的4-氰基苯磺酰胺在硫醇和碱的作用下干净地裂解成母体胺。该特征很容易使该基序在更广泛的胺合成范围内用作胺保护/活化基团。类似于磺基硝基苯磺酰胺，可以通过烷基化和芳基化进一步修饰结晶磺酰胺。磺酰胺类药物可以承受使硝基芳烃官能化的条件，例如还原反应和亲核取代反应。
• Amino acids and peptides. IX. Synthesis of cysteine-containing peptide fragments related to human hepatic metallothionein II (hMT II) and determination of their heavy metal-binding properties.
  作者：NORIYA OHTA、YOSHIO OKADA、KEIICHI TANAKA

  DOI：10.1248/cpb.31.3094

  日期：——

  Eight kinds of cysteine-containing peptides related to human hepatic metallothionein were synthesized by conventional methods. The metal-binding properties of these peptides with Zn2+ and Cd2+ were indicated by an increase of ultraviolet absorbance resulting from mercaptide formation. The Cd-binding activities of various peptides obtained here were assessed by measuring the increase in absorbance of mercaptide at 250 nm as a function of the concentration of Cd. The binding abilities of the peptides with Cd differed substancially.

  采用传统方法合成了八种与人类肝脏金属硫蛋白相关的含半胱氨酸肽。这些肽与 Zn2+ 和 Cd2+ 的金属结合特性是通过巯基的形成导致紫外吸光度的增加来显示的。通过测量 250 纳米波长处硫醇吸光度的增加与镉浓度的函数关系，评估了在此获得的各种多肽的镉结合活性。肽与镉的结合能力有很大差异。
• Amino acids and peptides. XXIV. Synthesis of Neurospora crassa metallothionein and related cysteine-containing peptides and examination of their heavy metal-binding properties.
  作者：Yoshio OKADA、Yutaka MATSUNO、Yasuhiro NSHIYAMA、Yuko TSUDA、Shin IGUCHI、Kyong-Son MIN、Satomi ONOSAKA、Keiichi TANAKA

  DOI：10.1248/cpb.37.2322

  日期：——

  corresponding to the entire amino acid sequence of Neurospora crassa metallothionein and several related cysteine-containing peptides were synthesized by the conventional solution method and their heavy metal-binding properties were examined. The Cu2+- or Cu+-binding properties of the various peptides were similar to each other, whereas the Cd2+-binding properties of these peptides were fairly structure-dependent

  通过常规溶液法合成了与芥菜神经孢菌金属硫蛋白的整个氨基酸序列相对应的五肽和几种相关的含半胱氨酸的肽，并检查了它们的重金属结合特性。各种肽的Cu2 +或Cu +结合性质彼此相似，而这些肽的Cd2 +结合性质是相当结构依赖性的。