6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine | 916154-77-3

• 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: 6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine
• 英文别名: N-[9-[(3aR,4R,6R,6aR)-6-ethenyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-yl]-N-benzoylbenzamide
• CAS: 916154-77-3
• 化学式: C₂₈H₂₅N₅O₅
• 分子量: 511.537
• InChiKey: IQOYFZHLVDGGPM-BMWKMAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine 在 Hoveyda-Grubbs catalyst second generation 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 50.5h， 生成 methyl 2-amino-5(E)-[5'-deoxyadenosin-5'-ylidene]pentanoate
  参考文献：
  名称：

  S-Adenosylhomocysteine Analogues with the Carbon-5‘ and Sulfur Atoms Replaced by a Vinyl Unit

  摘要：

  Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo) vinyl analogue.

  DOI：

  10.1021/ol062026m
• 作为产物：
  描述：

  5'-deoxy-2',3'-O-isopropylidene-5'-methyleneadenosine 、 苯甲酰氯 在 吡啶 作用下， 以97%的产率得到6-N,N-dibenzoyl-5'-deoxy-5'-methylene-2,3-O-isopropylideneadenosine
  参考文献：
  名称：

  S-Adenosylhomocysteine Analogues with the Carbon-5‘ and Sulfur Atoms Replaced by a Vinyl Unit

  摘要：

  Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo) vinyl analogue.

  DOI：

  10.1021/ol062026m

文献信息

• <i>S-</i>Adenosylhomocysteine Analogues with the Carbon-5‘ and Sulfur Atoms Replaced by a Vinyl Unit
  作者：Daniela Andrei、Stanislaw F. Wnuk

  DOI：10.1021/ol062026m

  日期：2006.10.1

  Cross-metathesis of suitably protected 5'-deoxy-5'-methyleneadenosines with racemic and chiral N-Boc-protected six-carbon amino acids bearing a terminal double bond in the presence of the Hoveyda-Grubbs catalyst gave adenosylhomocysteine analogues with the C5'-C6' double bond. Bromination with pyridinium tribromide and dehydrobromination with DBU followed by standard deprotections yielded the 5'-(bromo) vinyl analogue.