3'-fluoro-3'-deoxythymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite | 161006-80-0

• 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'-fluoro-3'-deoxythymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite
• 英文别名: N(iPr)2P(OCH2CH2CN)(-5)2-deoxy-D-eryPenf3F(b)-thymin-1-yl；3-[[di(propan-2-yl)amino]-[[(2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphanyl]oxypropanenitrile
• CAS: 161006-80-0
• 化学式: C₁₉H₃₀FN₄O₅P
• 分子量: 444.443
• InChiKey: QEUBPBGWZGTGMW-RPXCWWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3'-fluoro-3'-deoxythymidine-5'-(2-cyanoethyl diisopropylamino) phosphoramidite 在 四氮唑 、 甲醇 、 氨 、 碘 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 3'-fluoro-3'-deoxythymidine-5'-(ammonium methoxyphenylalaninyl) 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 、 3’-脱氧-3-氟胸苷 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以96%的产率得到3'-fluoro-3'-deoxythymidine-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

• A Phosphoramidite-Based Synthesis of Phosphoramidate Amino Acid Diesters of Antiviral Nucleosides
  作者：Timothy W. Abraham、Carston R. Wagner

  DOI：10.1080/15257779408010671

  日期：1994.9

  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.