((E)-(S)-3,4-Dihydroxy-but-1-enyl)-phosphonic acid diethyl ester | 174746-20-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: ((E)-(S)-3,4-Dihydroxy-but-1-enyl)-phosphonic acid diethyl ester
• CAS: 174746-20-4
• 化学式: C₈H₁₇O₅P
• 分子量: 224.194
• InChiKey: KMMUDZZKSUPWFG-GJIOHYHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  14.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((E)-(S)-3,4-Dihydroxy-but-1-enyl)-phosphonic acid diethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 三乙基硼 、 三正丁基氢锡 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 生成 [(2S,3S,5S)-2-Hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl]-phosphonic acid diethyl ester
  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：

  在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 ((E)-(S)-3,4-Dihydroxy-but-1-enyl)-phosphonic acid diethyl ester
  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