dimethyl 6-N-benzoyl-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonate | 1312544-67-4

• 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: dimethyl 6-N-benzoyl-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonate
• 英文别名: N-[9-[(2R,3R)-5-[[dimethoxy(oxido)phosphaniumyl]-hydroxymethyl]-3-hydroxy-2,3-dihydrofuran-2-yl]purin-6-yl]benzamide
• CAS: 1312544-67-4
• 化学式: C₁₉H₂₀N₅O₇P
• 分子量: 461.371
• InChiKey: UXVOLEQLUJPXSU-SDLZTHIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  164
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6-N-benzoyl-2',3'-O-methoxymethyleneadenosine 在 吡啶 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 dimethyl 6-N-benzoyl-3'-deoxy-3',4'-didehydroadenosine-5'-C-phosphonate 、
  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

文献信息

• 5′-Epimeric 3′-deoxy-3′,4′-didehydronucleoside-5′-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses
  作者：Magdalena Petrová、Miloš Buděšínský、Blanka Klepetářová、Ivan Rosenberg

  DOI：10.1016/j.tet.2011.04.037

  日期：2011.6

  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.