bis-(2-cyanoethyl) 6-N-benzoyl-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonate | 1312544-69-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: bis-(2-cyanoethyl) 6-N-benzoyl-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonate
• 英文别名: N-[9-[(2R,3R)-5-[[bis(2-cyanoethoxy)-oxidophosphaniumyl]-hydroxymethyl]-3-hydroxy-2,3-dihydrofuran-2-yl]purin-6-yl]benzamide
• CAS: 1312544-69-6
• 化学式: C₂₃H₂₂N₇O₇P
• 分子量: 539.444
• InChiKey: NBCYWSSMUQXELG-SOJKGPRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  212
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis-(2-cyanoethyl) 6-N-benzoyl-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonate 在 甲胺 作用下， 以 乙醇 为溶剂， 生成 (5'R)-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonic acid sodium salt 、 (5'S)-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonic acid sodium salt
  参考文献：
  名称：

  5′-Epimeric 3′-deoxy-3′,4′-didehydronucleoside-5′-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses

  摘要：

  Epimeric 5'-(RS) dialkyl 3'-deoxy-3',4'-didehydro-5'-C-phosphonates were prepared by nucleophilic addition of various dialkyl phosphites to 3'-deoxy-3',4'-didehydronucleoside-5'-aldehydes. Whereas direct NMR configuration assignment for the C5' atom bearing the phosphoryl and hydroxy groups using the J (P,H4') and J (H5',H4') coupling constants is impossible due to the absence of the H4' atom, successful separation, crystallisation and X-ray crystallographic analysis of a pair of epimeric 5'-C-phosphonates, followed by correlation with a series of NMR parameters, led to efficacious configuration assignment of individual epimers in the mixtures. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.04.037