(2R,3R,4R,5R)-2-((((allyloxy)(2-methoxy-2-oxoethoxy)phosphoryl)oxy)methyl)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate | 546113-78-4

• 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: (2R,3R,4R,5R)-2-((((allyloxy)(2-methoxy-2-oxoethoxy)phosphoryl)oxy)methyl)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate
• CAS: 546113-78-4
• 化学式: C₃₆H₃₄N₃O₁₃P
• 分子量: 747.652
• InChiKey: ATNQAAWLGTVANS-BWCNKMOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  53.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  196.88
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-((((allyloxy)(2-methoxy-2-oxoethoxy)phosphoryl)oxy)methyl)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate 在 吗啉 、 四(三苯基膦)钯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 {[(2R,3S,4R,5R)-5-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-hydroxy-phosphoryloxy}-acetic acid methyl ester
  参考文献：
  名称：

  Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases

  摘要：

  Several phosphoramidate analogues of CMP-N-acetylneuraminic acid were prepared for evaluation as inhibitors of alpha-2,3- and alpha-2,6-sialyltransferase. Central to the synthesis was the oxidative coupling of an amino acid ester with an H-phosphonate to construct the phosphoramidate linkage. All compounds synthesized were weak inhibitors of both of the sialyltransferases as determined by an HPLC-based inhibition assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00735-7
• 作为产物：
  描述：

  羟乙酸甲酯 、 3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite 在 四氮唑 、 二甲基二环氧乙烷 作用下， 以 乙腈 、 二氯甲烷 为溶剂， 以78%的产率得到(2R,3R,4R,5R)-2-((((allyloxy)(2-methoxy-2-oxoethoxy)phosphoryl)oxy)methyl)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases

  摘要：

  Several phosphoramidate analogues of CMP-N-acetylneuraminic acid were prepared for evaluation as inhibitors of alpha-2,3- and alpha-2,6-sialyltransferase. Central to the synthesis was the oxidative coupling of an amino acid ester with an H-phosphonate to construct the phosphoramidate linkage. All compounds synthesized were weak inhibitors of both of the sialyltransferases as determined by an HPLC-based inhibition assay. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00735-7