5-ethyl-1-[(2S,3R,4S,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)thiolan-2-yl]-3-(2-methoxyethoxymethyl)pyrimidine-2,4-dione | 316137-92-5

• 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: 5-ethyl-1-[(2S,3R,4S,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)thiolan-2-yl]-3-(2-methoxyethoxymethyl)pyrimidine-2,4-dione
• CAS: 316137-92-5
• 化学式: C₂₉H₃₆N₂O₇S
• 分子量: 556.68
• InChiKey: MEUNEJUIQIGQIY-LHWXFDGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-ethyl-1-[(2S,3R,4S,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)thiolan-2-yl]-3-(2-methoxyethoxymethyl)pyrimidine-2,4-dione 在 potassium fluoride 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 以80 mg的产率得到5-ethyl-1-[(R)-fluoro-[(2S,3R,4R)-3-phenylmethoxy-4-(phenylmethoxymethyl)thietan-2-yl]methyl]-3-(2-methoxyethoxymethyl)pyrimidine-2,4-dione
  参考文献：
  名称：

  2,2′-Anhydro-4′-Thionucleosides: Precursors for 2′-Azido- and 2′-Chloro-4′-thionucleosides and for a Novel Thiolane to Thietane Rearrangement

  摘要：

  2,2'-Anhydro-4'-thio-beta- and alpha -nucleosides 9 and 10 have been prepared by an in situ 4-thio-1,2-glycal addition route. They undergo ring-opening by azide or chloride ion to give, after deprotection, the 2'-substituted-4'-thionucleosides 13 and 14, whereas reactions with cyanide or fluoride sources lead to the unsaturated nucleosides 17 or 18, depending upon conditions. An unexpected and clean rearrangement to the thietane 23 occurs on treatment of uracil derivative 20 with DAST.

  DOI：

  10.1080/15257770008033855
• 作为产物：
  描述：

  (2S,4R,5S,6R)-11-ethyl-5-phenylmethoxy-4-(phenylmethoxymethyl)-7-oxa-3-thia-1,9-diazatricyclo[6.4.0.02,6]dodeca-8,11-dien-10-one 在 potassium fluoride 、 三乙胺 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-ethyl-1-[(2S,3R,4S,5R)-3-hydroxy-4-phenylmethoxy-5-(phenylmethoxymethyl)thiolan-2-yl]-3-(2-methoxyethoxymethyl)pyrimidine-2,4-dione
  参考文献：
  名称：

  2,2′-Anhydro-4′-Thionucleosides: Precursors for 2′-Azido- and 2′-Chloro-4′-thionucleosides and for a Novel Thiolane to Thietane Rearrangement

  摘要：

  2,2'-Anhydro-4'-thio-beta- and alpha -nucleosides 9 and 10 have been prepared by an in situ 4-thio-1,2-glycal addition route. They undergo ring-opening by azide or chloride ion to give, after deprotection, the 2'-substituted-4'-thionucleosides 13 and 14, whereas reactions with cyanide or fluoride sources lead to the unsaturated nucleosides 17 or 18, depending upon conditions. An unexpected and clean rearrangement to the thietane 23 occurs on treatment of uracil derivative 20 with DAST.

  DOI：

  10.1080/15257770008033855

文献信息

• 2,2′-Anhydro-4′-Thionucleosides: Precursors for 2′-Azido- and 2′-Chloro-4′-thionucleosides and for a Novel Thiolane to Thietane Rearrangement
  作者：J. Allen Miller、Ashley W. Pugh、G. Mustafa Ullah

  DOI：10.1080/15257770008033855

  日期：2000.9

  2,2'-Anhydro-4'-thio-beta- and alpha -nucleosides 9 and 10 have been prepared by an in situ 4-thio-1,2-glycal addition route. They undergo ring-opening by azide or chloride ion to give, after deprotection, the 2'-substituted-4'-thionucleosides 13 and 14, whereas reactions with cyanide or fluoride sources lead to the unsaturated nucleosides 17 or 18, depending upon conditions. An unexpected and clean rearrangement to the thietane 23 occurs on treatment of uracil derivative 20 with DAST.