1-(2'-deoxy-3'-O-(2-chlorophenyl2-cyanoethyl)-phosphate-β-D-erythro-ribofuranosyl)-2-thiouracil | 152753-95-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 1-(2'-deoxy-3'-O-(2-chlorophenyl2-cyanoethyl)-phosphate-β-D-erythro-ribofuranosyl)-2-thiouracil
• 英文别名: 1-[2'-deoxy-3'-O-(2-chlorophenyl2-cyanoethyl)-phosphate-β-D-erythro-ribofuranosyl]-2-thiouracil
• CAS: 152753-95-2
• 化学式: C₁₈H₁₉ClN₃O₇PS
• 分子量: 487.858
• InChiKey: OLIAIZHQTBUBTM-FCHKPPAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  31.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  135.8
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-(2'-deoxy-3'-O-(2-chlorophenyl2-cyanoethyl)-phosphate-β-D-erythro-ribofuranosyl)-2-thiouracil 在 吡啶 、 N-甲基咪唑 、 2,4,6-三异丙基苯磺酰氯 、 syn-2-pyridinealdoxime 、 水 、 溶剂黄146 、 四甲基胍 作用下， 反应 29.55h， 生成
  参考文献：
  名称：

  A Stereoselective Synthesis of α - and β-2′-Deoxy-2-thiouridine

  摘要：

  A stereoselective glycosylation procedure is described for the synthesis of protected alpha- and beta-2'-deoxy-2-thiouridine (dS2U) in 68% and 94% yield, respectively. Evidence is presented that suggests the reaction proceeds through a silylated thioglycoside intermediate. This intermediate undergoes an efficient S2-->N1 rearrangement mediated by SnCl4. The phosphoramidite and phosphodiester synthons and a dS2U dinucleotide are also synthesized and the X-ray structure of beta-dS2U is presented.

  DOI：

  10.1080/07328319308021507
• 作为产物：
  描述：

  2-硫代2'-脱氧尿苷 在 吡啶 、 N-甲基咪唑 、 二氯乙酸 、 4-二甲氨基吡啶 、 2,4,6-三异丙基苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 7.78h， 生成 1-(2'-deoxy-3'-O-(2-chlorophenyl2-cyanoethyl)-phosphate-β-D-erythro-ribofuranosyl)-2-thiouracil
  参考文献：
  名称：

  A Stereoselective Synthesis of α - and β-2′-Deoxy-2-thiouridine

  摘要：

  A stereoselective glycosylation procedure is described for the synthesis of protected alpha- and beta-2'-deoxy-2-thiouridine (dS2U) in 68% and 94% yield, respectively. Evidence is presented that suggests the reaction proceeds through a silylated thioglycoside intermediate. This intermediate undergoes an efficient S2-->N1 rearrangement mediated by SnCl4. The phosphoramidite and phosphodiester synthons and a dS2U dinucleotide are also synthesized and the X-ray structure of beta-dS2U is presented.

  DOI：

  10.1080/07328319308021507