3',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine | 155807-20-8

• 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',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine
• 英文别名: Tos(-3)[Tos(-5)]2-deoxy-D-eryPenf(b)-uracil-1-yl；[(2R,3S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-(4-methylphenyl)sulfonyloxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 155807-20-8
• 化学式: C₂₃H₂₄N₂O₉S₂
• 分子量: 536.584
• InChiKey: FNXPWAMYIJENAG-TUNNFDKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine 以 乙醇 为溶剂， 反应 48.17h， 生成 1-(3,5-anhydro-2-deoxy-β-D-threo-pentofuranosyl)-2-N-methylisocytosine
  参考文献：
  名称：

  Synthesis of some 2′,3′-didehydro-2′,3′-dideoxynucleosides derived from modified pyrimidine bases

  摘要：

  3'.5'-Bis-O-(4-tolylsulfonyl)-thymidine and -2'-deoxyuridine (13a and 13b) reacted with sodium ethoxide in boiling ethanol to give the corresponding ethoxy-oxetanes 12a and 12b in 67 and 66% overall yield for the two-step processes starting from thymidine 4a and 2'-deoxyuridine 4b; respectively. Treatment of the ethoxy-oxetanes 12a and 12b with hydrogen sulfide and N-1,N-1,N-3,N-3- tetramethylguanidine in dry pyridine solution gave the 2-thiothymine- and 2-thiouracil-derived oxetanes 19a and 19b in 62 and 68.5% yield, respectively. When the latter compounds were treated with potassium tert-butoxide in dimethyl sulfoxide, the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides (d4 nucleosides) 10a and 10b were obtained in 66 and 60% yield. respectively. The 2-thiothymine-derived oxetane 19a was converted via the 5-methyl-2-thiocytosine-derived oxetane 21a into the 5-methyl-2-thiocytosine-derived d4 nucleoside 11a in 59.5% overall yield; the 2-thiouracil-derived oxetane 19b was similarly converted into the 2-thiocytosine- and 4-N-methyl-2-thiocytosine-derived d4 nucleosides 11b and 23 in 51 and 50% overall yield, respectively. Finally, the ethoxy-oxetane 12b was converted into the corresponding amino- and methylamino-oxetanes 25a and 25b in 74 and 83% yield, respectively. The latter compound. 25b, was successfully converted into the 2-N-methylisocytosine-derived d4 nucleoside 26b in 62% yield.

  DOI：

  10.1039/p19940000189
• 作为产物：
  描述：

  4-甲苯磺酸酐 、 2-脱氧尿苷 在 吡啶 作用下， 反应 0.17h， 以6.37 g的产率得到3',5'-bis-O-(4-tolylsulfonyl)-2'-deoxyuridine
  参考文献：
  名称：

  Synthesis of some 2′,3′-didehydro-2′,3′-dideoxynucleosides derived from modified pyrimidine bases

  摘要：

  3'.5'-Bis-O-(4-tolylsulfonyl)-thymidine and -2'-deoxyuridine (13a and 13b) reacted with sodium ethoxide in boiling ethanol to give the corresponding ethoxy-oxetanes 12a and 12b in 67 and 66% overall yield for the two-step processes starting from thymidine 4a and 2'-deoxyuridine 4b; respectively. Treatment of the ethoxy-oxetanes 12a and 12b with hydrogen sulfide and N-1,N-1,N-3,N-3- tetramethylguanidine in dry pyridine solution gave the 2-thiothymine- and 2-thiouracil-derived oxetanes 19a and 19b in 62 and 68.5% yield, respectively. When the latter compounds were treated with potassium tert-butoxide in dimethyl sulfoxide, the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides (d4 nucleosides) 10a and 10b were obtained in 66 and 60% yield. respectively. The 2-thiothymine-derived oxetane 19a was converted via the 5-methyl-2-thiocytosine-derived oxetane 21a into the 5-methyl-2-thiocytosine-derived d4 nucleoside 11a in 59.5% overall yield; the 2-thiouracil-derived oxetane 19b was similarly converted into the 2-thiocytosine- and 4-N-methyl-2-thiocytosine-derived d4 nucleosides 11b and 23 in 51 and 50% overall yield, respectively. Finally, the ethoxy-oxetane 12b was converted into the corresponding amino- and methylamino-oxetanes 25a and 25b in 74 and 83% yield, respectively. The latter compound. 25b, was successfully converted into the 2-N-methylisocytosine-derived d4 nucleoside 26b in 62% yield.

  DOI：

  10.1039/p19940000189

文献信息

• Synthesis of some 2′,3′-didehydro-2′,3′-dideoxynucleosides derived from modified pyrimidine bases
  作者：Colin B. Reese、Chamakura V. N. S. Varaprasad

  DOI：10.1039/p19940000189

  日期：——

  3'.5'-Bis-O-(4-tolylsulfonyl)-thymidine and -2'-deoxyuridine (13a and 13b) reacted with sodium ethoxide in boiling ethanol to give the corresponding ethoxy-oxetanes 12a and 12b in 67 and 66% overall yield for the two-step processes starting from thymidine 4a and 2'-deoxyuridine 4b; respectively. Treatment of the ethoxy-oxetanes 12a and 12b with hydrogen sulfide and N-1,N-1,N-3,N-3- tetramethylguanidine in dry pyridine solution gave the 2-thiothymine- and 2-thiouracil-derived oxetanes 19a and 19b in 62 and 68.5% yield, respectively. When the latter compounds were treated with potassium tert-butoxide in dimethyl sulfoxide, the corresponding 2',3'-didehydro-2',3'-dideoxynucleosides (d4 nucleosides) 10a and 10b were obtained in 66 and 60% yield. respectively. The 2-thiothymine-derived oxetane 19a was converted via the 5-methyl-2-thiocytosine-derived oxetane 21a into the 5-methyl-2-thiocytosine-derived d4 nucleoside 11a in 59.5% overall yield; the 2-thiouracil-derived oxetane 19b was similarly converted into the 2-thiocytosine- and 4-N-methyl-2-thiocytosine-derived d4 nucleosides 11b and 23 in 51 and 50% overall yield, respectively. Finally, the ethoxy-oxetane 12b was converted into the corresponding amino- and methylamino-oxetanes 25a and 25b in 74 and 83% yield, respectively. The latter compound. 25b, was successfully converted into the 2-N-methylisocytosine-derived d4 nucleoside 26b in 62% yield.