3'-azido-3'-deoxy-5'-thymidinyl 6-D-(+)-mannopyranosyl thiophosphate

• 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: 3'-azido-3'-deoxy-5'-thymidinyl 6-D-(+)-mannopyranosyl thiophosphate
• 英文别名: 1-[(2R,4S,5S)-4-azido-5-[[hydroxy-[[(2R,3S,4S,5S)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy]phosphinothioyl]oxymethyl]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₆H₂₄N₅O₁₁PS
• 分子量: 525.433
• InChiKey: SMUOJPMLCFHIBD-FJVKHQHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  234
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  甘露糖 、 齐多夫定 在 四氮唑 、 acetamidomethyl NovaGel^TM-2-iPr₂N-1,3,2-oxathiaphospholane 、 苯基二硫化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 40.0h， 以47%的产率得到3'-azido-3'-deoxy-5'-thymidinyl 6-D-(+)-mannopyranosyl thiophosphate
  参考文献：
  名称：

  Solid-Phase Synthesis of Dinucleoside and Nucleoside-Carbohydrate Phosphodiesters and Thiophosphodiesters

  摘要：

  Unprotected nucleosides (ROH) were reacted with two polymers bound to N, N-diisopropylamino- 1,3,2-oxathiaphospholane in the presence of 1H-terazole. Oxidation with tertbutyl hydroperoxide or sulfurization with Beaucage's reagent, followed by the 1,3,2-oxathiaphospholane ring opening with unprotected nucleosides or carbohydrates (R'OH) in the presence of DBU, afforded nucleoside-(5'-5')-nucleoside or nucleoside- carbohydrate phosphodiester and thiophosphodiester derivatives through the elimination of polymer-bound ethylene episulfide. This strategy offers the advantages of facile isolation of final products and monosubstitution of unprotected nucleosides and carbohydrates.

  DOI：

  10.1021/jo0611115