N-3-tert-butoxycarbonyl-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil | 1454611-75-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N-3-tert-butoxycarbonyl-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil
• 英文别名: tert-butyl 3-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(2R)-oxiran-2-yl]-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,6-dioxopyrimidine-1-carboxylate
• CAS: 1454611-75-6
• 化学式: C₁₈H₂₄N₂O₈
• 分子量: 396.397
• InChiKey: FTVQNRCMIZFIEI-DKTYCGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-3-tert-butoxycarbonyl-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil 在 三甲基氯硅烷 、 水 、 三乙胺 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 1-(5S)-[6-deoxy-6-diethylphosphono-β-D-ribohexofuranosyl]uracil
  参考文献：
  名称：

  An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs

  摘要：

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.

  DOI：

  10.1021/ol402143y
• 作为产物：
  描述：

  1-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)uracil 在 吡啶 、 4-二甲氨基吡啶 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.25h， 生成 N-3-tert-butoxycarbonyl-1-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuranosyl)uracil
  参考文献：
  名称：

  An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs

  摘要：

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.

  DOI：

  10.1021/ol402143y

文献信息

• An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs
  作者：Audrey Hospital、Maïa Meurillon、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1021/ol402143y

  日期：2013.9.20

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.