(methoxyamino)acetic acid benzyl ester

• 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: (methoxyamino)acetic acid benzyl ester
• 英文别名: benzyl (2-methoxyamino)acetate；Benzyl 2-(methoxyamino)acetate；benzyl 2-(methoxyamino)acetate
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: RLKWRUATHZDASJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (methoxyamino)acetic acid benzyl ester 、 二碳酸二叔丁酯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以96%的产率得到benzyl [N-tert-butoxycarbonyl-N-methoxyamino]acetate
  参考文献：
  名称：

  Colchicine Glycorandomization Influences Cytotoxicity and Mechanism of Action

  摘要：

  The reaction of 70 unprotected, diversely functionalized free reducing sugars with methoxyamine-appended colchicine led to the production of a 58-member glycorandomized library. High-throughput cytotoxicity assays revealed glycosylation to modulate specificity and potency. Library members were also identified which, unlike the parent natural product (a destabilizer), stabilized in vitro tubulin polymerization in a manner similar to taxol. This study highlights a simple extension of neoglycorandomization toward amine-bearing scaffolds and the potential benefit of glycosylating nonglycosylated natural products.

  DOI：

  10.1021/ja064686s
• 作为产物：
  描述：

  (methoxyimino)acetic acid benzyl ester 在 盐酸 、 吡啶硼烷 作用下， 以 吡啶 、 乙醇 为溶剂， 以88%的产率得到(methoxyamino)acetic acid benzyl ester
  参考文献：
  名称：

  Colchicine Glycorandomization Influences Cytotoxicity and Mechanism of Action

  摘要：

  The reaction of 70 unprotected, diversely functionalized free reducing sugars with methoxyamine-appended colchicine led to the production of a 58-member glycorandomized library. High-throughput cytotoxicity assays revealed glycosylation to modulate specificity and potency. Library members were also identified which, unlike the parent natural product (a destabilizer), stabilized in vitro tubulin polymerization in a manner similar to taxol. This study highlights a simple extension of neoglycorandomization toward amine-bearing scaffolds and the potential benefit of glycosylating nonglycosylated natural products.

  DOI：

  10.1021/ja064686s

文献信息

• [EN] COLCHICINE NEOGLYCOSIDES AND METHODS FOR THEIR SYNTHESIS AND USE<br/>[FR] NÉOGLYCOSIDES DE COLCHICINE ET PROCÉDÉS POUR LEUR SYNTHÈSE ET UTILISATION
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2008067039A3

  公开（公告）日：2008-08-14