N-Boc-valine vinyl ester | 1154062-75-5

• 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-Boc-valine vinyl ester
• 英文别名: ethenyl (2S)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 1154062-75-5
• 化学式: C₁₂H₂₁NO₄
• 分子量: 243.303
• InChiKey: KARCUNJIAYQMQT-VIFPVBQESA-N

物化性质

• 沸点：
  316.7±25.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Boc-valine vinyl ester 在 吡啶 、 Bacillus subtilis subtilisin 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Novel l-amino acid ester prodrugs of azacitidine: Design, enzymatic synthesis and the investigation of release behavior

  摘要：

  A facile, enzymatic synthesis protocol of L-amino acid ester prodrugs of azacitidine was developed. Firstly, transesterification of azacitidine with Boc protected vinyl aminocarboxylates was performed under the catalysis of subtilisin in anhydrous pyridine at 50 degrees C. A series of Boc-protected amino acid-azacitidine conjugates were prepared in good regioselectivity and yield. Various factors which influence the catalytic efficiency were systematically investigated. And then, the obtained azacitidine derivatives were subjected to a deprotection process to give L-amino acid ester prodrugs of azacitidine. In vitro hydrolysis of prodrugs showed that the amino acid ester prodrugs had obvious sustained release characteristic. These characteristics will have potential value for clinic application. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.03.018
• 作为产物：
  描述：

  乙酸乙烯酯 、 N-Boc-L-缬氨酸 在 palladium diacetate 、 potassium hydroxide 作用下， 反应 24.0h， 以77%的产率得到N-Boc-valine vinyl ester
  参考文献：
  名称：

  用于从生物拆分物中分离对映异构体的酸洗标签的开发

  摘要：

  已经开发出一种分离工具，该分离工具涉及在生物拆分中使用乙烯基酯氨基酸作为酰基供体。可酸洗的酰基充当可去除的标签，有助于将仲醇从生物拆分产物混合物中分离出来。这些酰基供体来自廉价，可商购的氨基酸，已证明与水解酶南极假丝酵母脂肪酶B一起用于各种仲醇的选择性酰化中。

  DOI：

  10.1021/op900028d

文献信息

• 一种阿糖胞苷5’-O-L-缬氨酸酯盐酸盐的制 备方法
  申请人：昆明积大制药股份有限公司

  公开号：CN105273023B

  公开（公告）日：2018-11-06

  本发明提供一种阿糖胞苷5’‑O‑L‑缬氨酸酯盐酸盐（结构式1）及其中间体的制备方法。该方法以阿糖胞苷（式5）为原料，经一步反应保护氨基得到结构式3，再与N’‑叔丁氧羰基‑L‑缬氨酸在碱存在下与氯甲酸酯或酰氯反应，或与N’‑叔丁氧羰基‑L‑缬氨酸盐在氯甲酸酯或酰氯作用下进行酯化反应得到结构式2，然后在氯化氢作用下脱去保护基得到结构式1。该方法具有反应易于操作、后处理简单、无需柱层析纯化、选择性高、反应收率高、成本低、适于工业化生产的特点。
• DEGRADABLE POLYCATIONS DERIVED FROM AMINO ACID VINYL ESTERS
  申请人：Wisconsin Alumini Research Foundation

  公开号：US20130184423A1

  公开（公告）日：2013-07-18

  Described herein are the synthesis and polymerization of a series of N-Boc-protected amino acid vinyl ester (BAAVE) monomers. Homopolymers and heteropolymers containing the monomers are described, particularly heteropolymers with vinyl ester monomers such as vinyl acetate. Deprotection can be used to produce hydrophilic and hydrophobic polymers that are particular useful in biological applications such as cellular delivery of biological materials.
• US8796405B2
  申请人：——

  公开号：US8796405B2

  公开（公告）日：2014-08-05
• US9688789B2
  申请人：——

  公开号：US9688789B2

  公开（公告）日：2017-06-27
• Novel l-amino acid ester prodrugs of azacitidine: Design, enzymatic synthesis and the investigation of release behavior
  作者：Fan Xu、Ming Zhang、Qi Wu、Xianfu Lin

  DOI：10.1016/j.molcatb.2014.03.018

  日期：2014.7

  A facile, enzymatic synthesis protocol of L-amino acid ester prodrugs of azacitidine was developed. Firstly, transesterification of azacitidine with Boc protected vinyl aminocarboxylates was performed under the catalysis of subtilisin in anhydrous pyridine at 50 degrees C. A series of Boc-protected amino acid-azacitidine conjugates were prepared in good regioselectivity and yield. Various factors which influence the catalytic efficiency were systematically investigated. And then, the obtained azacitidine derivatives were subjected to a deprotection process to give L-amino acid ester prodrugs of azacitidine. In vitro hydrolysis of prodrugs showed that the amino acid ester prodrugs had obvious sustained release characteristic. These characteristics will have potential value for clinic application. (C) 2014 Elsevier B.V. All rights reserved.