(2S,3R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl (2S)-2-amino-3-methylbutanoate

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (2S,3R,5S)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl (2S)-2-amino-3-methylbutanoate
• 英文别名: [5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl] 2-amino-3-methylbutanoate
• 化学式: C₁₄H₂₂N₄O₅
• 分子量: 326.35
• InChiKey: VFCYZPOEGWLYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  6

文献信息

• Industrially scalable nucleoside synthesis
  申请人：Moussa Adel

  公开号：US20050004357A1

  公开（公告）日：2005-01-06

  An industrially scalable two-step process for preparing a β-L-2′-deoxy-nucleoside that results in a predominance of the β- over the γ-anomeric form of the compound is described. An optional third step may be used to prepare 3′-prodrugs of desirable β-L-2′-deoxy-nucleosides for the delivery of these pharmaceuticals effective for treating viral diseases. The synthetic process is applicable in particular to the formation of β-L-2′-deoxy-cytidine, a pharmaceutically acceptable salt or prodrug thereof. The process can provide a relatively uncontaminated product that may require no further isolation or purification, thereby making the synthesis easily scalable for industrial manufacture.

  本文介绍了一种工业可扩展的两步法制备β-L-2'-去氧核苷的方法，该方法使化合物的β-异构体形式优于γ-异构体形式。第三步是可选的，可用于制备所需的β-L-2'-去氧核苷3'-前药，以便有效治疗病毒性疾病。该合成过程特别适用于形成β-L-2'-去氧胞苷，其药用盐或前药。该过程可以提供相对不受污染的产品，可能不需要进一步的分离或纯化，从而使合成易于工业生产规模化。
• INDUSTRIALLY SCALABLE NUCLEOSIDE SYNTHESIS
  申请人：Idenix (Cayman) Limited

  公开号：EP1620451A2

  公开（公告）日：2006-02-01
• EP1620451A4
  申请人：——

  公开号：EP1620451A4

  公开（公告）日：2009-02-18
• PRODRUGS OF DEOXYNUCLEOSIDES FOR TREATMENT OF DISEASES CASED BY UNBALANCED NUCLEOTIDE POOLS
  申请人：Modis Therapeutics, Inc.

  公开号：US20210077519A1

  公开（公告）日：2021-03-18

  Deoxynucleotide prodrugs for treatment of diseases characterized by unbalanced nucleotide pools are provided herein.
• US7595390B2
  申请人：——

  公开号：US7595390B2

  公开（公告）日：2009-09-29