1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-[2-(methoxycarbonyl)-vinyl]-uracil | 386747-71-3

• 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: 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-[2-(methoxycarbonyl)-vinyl]-uracil
• 英文别名: methyl (E)-3-[1-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-2,4-dioxopyrimidin-5-yl]prop-2-enoate
• CAS: 386747-71-3
• 化学式: C₁₃H₁₄N₂O₆
• 分子量: 294.264
• InChiKey: LEZJYRWBZFQHOJ-QOHYJFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  110.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,12-二氨基十二烷 、 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-[2-(methoxycarbonyl)-vinyl]-uracil 生成 (E)-N-(12-Amino-dodecyl)-3-[1-((2R,5S)-5-hydroxymethyl-2,5-dihydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acrylamide
  参考文献：
  名称：

  Synthesis of Novel C-5 Substituted d4t Analogues Bearing Linker Arms as Potential Anti-HIV Agents

  摘要：

  This work reports the synthesis of 2',3'-didehydro-2',3'-dideoxy-thymidine analogues bearing several kinds of amino-linker arms at the C-5 position of the pyrimidine moiety. C-5 is an attractive position since a flexible chain may permit the triphosphates to be generated. The beta-D- and beta-L-d4T analogues were synthesized following a multi-step reaction from D-ribose and D-xylose, from D- and L-arabinose (towards an oxazoline ring) or from uridine and then were reacted with alkylene diamines.

  DOI：

  10.1080/15257779908041592
• 作为产物：
  描述：

  1-(5-O-acetyl-2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-iodo-uracil 在 palladium diacetate 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 24.0h， 生成 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)-5-[2-(methoxycarbonyl)-vinyl]-uracil
  参考文献：
  名称：

  SYNTHESIS OF 5-ALKENYLATED D4T ANALOGUES VIA THE Pd-CATALYZED CROSS-COUPLING REACTION

  摘要：

  The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-uridine (12) and 5-{N-[5-(methoxycarbonyl)-pentyl]acrylamide}-2 ' ,3 ' -didehydro-2',3 ' -dideoxy-uridine (15) were prepared by the palladium acetate-triphenylphosphine-catalyzed reaction of the 5 ' -O-acetyl-5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screened for their anti-HIV activity. The biological data demonstrated that none of them were active against HIV-1.

  DOI：

  10.1081/ncn-100105902