4(S)-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-2(S)-(p-O-toluenesulfonylmethyl)tetrahydrofuran | 160999-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4(S)-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-2(S)-(p-O-toluenesulfonylmethyl)tetrahydrofuran
• 英文别名: [(2S,4S)-4-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 160999-14-4
• 化学式: C₁₆H₁₈N₂O₆S
• 分子量: 366.395
• InChiKey: BFNAWCDJYZPJQK-STQMWFEESA-N

物化性质

• 密度：
  1.392±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4(S)-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-2(S)-(p-O-toluenesulfonylmethyl)tetrahydrofuran 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以67%的产率得到O²,6'-anhydro-4(S)-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>tetrahydro-2(S)-furanmethanol
  参考文献：
  名称：

  Novel isomeric dideoxynucleosides as potential antiviral agents

  摘要：

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.

  DOI：

  10.1016/s0040-4020(01)85259-5
• 作为产物：
  描述：

  [(3aR,5S,6aR)-2,2-dimethyltetrhydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate 在 palladium on activated charcoal 盐酸 、 三乙基硅烷 、 三甲基氯硅烷 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 氢气 作用下， 以 吡啶 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 5.0~80.0 ℃ 、275.79 kPa 条件下， 反应 118.0h， 生成 4(S)-<3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl>-2(S)-(p-O-toluenesulfonylmethyl)tetrahydrofuran
  参考文献：
  名称：

  Novel isomeric dideoxynucleosides as potential antiviral agents

  摘要：

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.

  DOI：

  10.1016/s0040-4020(01)85259-5

文献信息

• Novel isomeric dideoxynucleosides as potential antiviral agents
  作者：Pascal J. Bolon、Todd B. Sells、Zoraida M. Nuesca、David F. Purdy、Vasu Nair

  DOI：10.1016/s0040-4020(01)85259-5

  日期：1994.1

  Novel isomeric dideoxynucleosides with S,S absolute stereochemistry and involving the transposition of the base moiety from the normal 1'- to the 2'-position have been regiospecifically and stereospecifically synthesized. The synthetic approaches involved either direct coupling with inversion at the 2-position of a preformed dideoxygenated sugar using the base moiety as nucleophile (for purine isodideoxynucleosides) or construction of the base moiety onto a stereochemically defined amino sugar precursor (pyrimidine isodideoxynucleosides). These compounds possess extremely high stability with respect to ''glycosidic'' bond cleavage and enzymatic deamination. Antiviral data suggest that the most active compound was levorotatory S,S-isodideoxyadenosine.