[(2S,3S,5R)-3-(diethoxyphosphinothioylmethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate | 213611-27-9

• 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: [(2S,3S,5R)-3-(diethoxyphosphinothioylmethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 213611-27-9
• 化学式: C₂₂H₂₉N₂O₇PS
• 分子量: 496.521
• InChiKey: WUPLQLDAXZUVFB-GUDVDZBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,3S,5R)-3-(diethoxyphosphinothioylmethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到1-(5-O-benzoyl-2,3-dideoxy-3-diethoxyphosphorylmethyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl)thymine
  参考文献：
  名称：

  Stereoselective β-N-glycosylation of 2,3-dideoxyribofuranose derivatives controlled by a methylenephosphonothioate functional group at the 3-position

  摘要：

  N-glycolylation of 3-(diethoxyphosphorothioyl)methyl-5-O-benzoyl-1-O-ethyl-2,3-dideoxyriboses 9b and 10b with silylated thymine in the presence of TiCl4 proceeded highly diastereoselectively (92% de) to give the corresponding beta-nucleotide analogues in good yield. A remarkable neighboring group participation of the methylenephosphonothioate functionality was observed in the course of the beta-N-glycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01335-5
• 作为产物：
  描述：

  [(E,2S)-2-(2-bromo-1-ethoxyethoxy)-4-diethoxyphosphinothioylbut-3-enyl] benzoate 在 N,O-双三甲硅基乙酰胺 、 三乙基硼 、 三正丁基氢锡 、 四氯化钛 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 [(2S,3S,5R)-3-(diethoxyphosphinothioylmethyl)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Stereoselective β-N-glycosylation of 2,3-dideoxyribofuranose derivatives controlled by a methylenephosphonothioate functional group at the 3-position

  摘要：

  N-glycolylation of 3-(diethoxyphosphorothioyl)methyl-5-O-benzoyl-1-O-ethyl-2,3-dideoxyriboses 9b and 10b with silylated thymine in the presence of TiCl4 proceeded highly diastereoselectively (92% de) to give the corresponding beta-nucleotide analogues in good yield. A remarkable neighboring group participation of the methylenephosphonothioate functionality was observed in the course of the beta-N-glycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01335-5

文献信息

• Stereoselective β-N-glycosylation of 2,3-dideoxyribofuranose derivatives controlled by a methylenephosphonothioate functional group at the 3-position
  作者：Tsutomu Yokomatsu、Tomoyuki Sada、Takanori Shimizu、Shiroshi Shibuya

  DOI：10.1016/s0040-4039(98)01335-5

  日期：1998.8

  N-glycolylation of 3-(diethoxyphosphorothioyl)methyl-5-O-benzoyl-1-O-ethyl-2,3-dideoxyriboses 9b and 10b with silylated thymine in the presence of TiCl4 proceeded highly diastereoselectively (92% de) to give the corresponding beta-nucleotide analogues in good yield. A remarkable neighboring group participation of the methylenephosphonothioate functionality was observed in the course of the beta-N-glycosylation. (C) 1998 Elsevier Science Ltd. All rights reserved.