3'-deoxy-2',3'-didehydrothymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite | 161006-81-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 3'-deoxy-2',3'-didehydrothymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite
• CAS: 161006-81-1
• 化学式: C₁₉H₂₉N₄O₅P
• 分子量: 424.437
• InChiKey: MMMRTZBJIGPSPV-KZKVIATDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  109.58
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3'-deoxy-2',3'-didehydrothymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite 在 四氮唑 、 甲醇 、 氨 、 碘 作用下， 以 甲醇 为溶剂， 生成 3'-deoxy-2',3'-didehydrothymidine-5'-(ammonium methoxytryptophanyl) phosphoramidate
  参考文献：
  名称：

  A Phosphoramidite-Based Synthesis of Phosphoramidate Amino Acid Diesters of Antiviral Nucleosides

  摘要：

  A general synthetic procedure is presented for the preparation of 5'-amino acid phosphoramidates of zidovudine (AZT), 3'-deoxy-2',3'-didehydrothymidine (D4T), and 3'-fluoro-3'-deoxythymidine (FLT) from their corresponding phosphoramidites. These water soluble amino acid phosphoramidates are more non-polar than the parent nucleoside and exhibit high stability in aqueous media.

  DOI：

  10.1080/15257779408010671
• 作为产物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 司他夫定 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 3'-deoxy-2',3'-didehydrothymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite
  参考文献：
  名称：

  A Phosphoramidite-Based Synthesis of Phosphoramidate Amino Acid Diesters of Antiviral Nucleosides

  摘要：

  A general synthetic procedure is presented for the preparation of 5'-amino acid phosphoramidates of zidovudine (AZT), 3'-deoxy-2',3'-didehydrothymidine (D4T), and 3'-fluoro-3'-deoxythymidine (FLT) from their corresponding phosphoramidites. These water soluble amino acid phosphoramidates are more non-polar than the parent nucleoside and exhibit high stability in aqueous media.

  DOI：

  10.1080/15257779408010671

文献信息

• Hydroxy fatty acids for the delivery of dideoxynucleosides as anti-HIV agents
  作者：Kishore Lingam Gangadhara、Eveline Lescrinier、Christophe Pannecouque、Piet Herdewijn

  DOI：10.1016/j.bmcl.2013.12.093

  日期：2014.2

  A series of alpha- and beta-carboxylated phospholipid prodrugs of dideoxy nucleosides have been synthesized and evaluated against HIV. An increase in biological effect with a factor of 500 has only been observed for the adenine nucleoside, which suggests that this prodrug approach is base specific. (C) 2014 Elsevier Ltd. All rights reserved.