[(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-[[[(2-methoxy-2-oxoethyl)amino]-oxido-prop-2-enoxyphosphaniumyl]oxymethyl]oxolan-3-yl] benzoate | 546113-66-0

• 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)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-[[[(2-methoxy-2-oxoethyl)amino]-oxido-prop-2-enoxyphosphaniumyl]oxymethyl]oxolan-3-yl] benzoate
• CAS: 546113-66-0
• 化学式: C₃₆H₃₅N₄O₁₂P
• 分子量: 746.667
• InChiKey: XVVAHGXAPSFKKF-BWCNKMOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  203
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-[[[(2-methoxy-2-oxoethyl)amino]-oxido-prop-2-enoxyphosphaniumyl]oxymethyl]oxolan-3-yl] benzoate 在 吗啉 、 sodium hydroxide 、 四(三苯基膦)钯 、 sodium methylate 、 三苯基膦 作用下， 以 甲醇 、 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-phosphorylamino}-acetic acid
  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：

  3-propenyl-(2',3'-O,N⁴-tribenzoyl cytidine-5')-yl-N,N'-diisopropylphosphoramidite 在 四氮唑 、 水 、 三乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 生成 [(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-4-benzoyloxy-2-[[[(2-methoxy-2-oxoethyl)amino]-oxido-prop-2-enoxyphosphaniumyl]oxymethyl]oxolan-3-yl] benzoate
  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

文献信息

• Synthesis and evaluation of phosphoramidate amino acid-based inhibitors of sialyltransferases
  作者：Lisa J. Whalen、Kerry A. McEvoy、Randall L. Halcomb

  DOI：10.1016/s0960-894x(02)00735-7

  日期：2003.1

  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.