Pentanedioic acid mono-[(2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester | 876403-52-0

• 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: Pentanedioic acid mono-[(2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester
• 英文别名: 5-[(2R,3S,5R)-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)-2-(prop-2-enoxymethyl)oxolan-3-yl]oxy-5-oxopentanoic acid
• CAS: 876403-52-0
• 化学式: C₂₅H₂₈N₂O₉
• 分子量: 500.505
• InChiKey: UPTXLXPBCKPGII-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Pentanedioic acid mono-[(2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 39.0h， 生成
  参考文献：
  名称：

  New Dinucleoside Analogues via Cross-Coupling Metathesis

  摘要：

  Synthesis of 3'-3', 5-5', and 3'-5' dimeric thymidine, linked by an olefinic chain between glycosidic moieties is described. Cross metathesis reaction of 3' or 5' O-allyl analogues of thymidine led to the expected 3'-3' and 5'-5' dimeric compounds, respectively. In order to obtain the 3'-5' dimer, 5'-O-allyl and 3'-O-allyl monomers were first linked by their free 3' OH and 5' OH groups through a glutaryl spacer; ring closing metathesis was then operated upon this temporary dimer, followed by glutaryl removal.

  DOI：

  10.1081/ncn-60595
• 作为产物：
  描述：

  5'-O-(prop-2-enyl)thymidine 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 Pentanedioic acid mono-[(2R,3S,5R)-2-allyloxymethyl-5-(3-benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester
  参考文献：
  名称：

  New Dinucleoside Analogues via Cross-Coupling Metathesis

  摘要：

  Synthesis of 3'-3', 5-5', and 3'-5' dimeric thymidine, linked by an olefinic chain between glycosidic moieties is described. Cross metathesis reaction of 3' or 5' O-allyl analogues of thymidine led to the expected 3'-3' and 5'-5' dimeric compounds, respectively. In order to obtain the 3'-5' dimer, 5'-O-allyl and 3'-O-allyl monomers were first linked by their free 3' OH and 5' OH groups through a glutaryl spacer; ring closing metathesis was then operated upon this temporary dimer, followed by glutaryl removal.

  DOI：

  10.1081/ncn-60595

文献信息

• New Dinucleoside Analogues via Cross-Coupling Metathesis
  作者：Vincent Roy、Rachida Zerrouki、Pierre Krausz

  DOI：10.1081/ncn-60595

  日期：2005.3

  Synthesis of 3'-3', 5-5', and 3'-5' dimeric thymidine, linked by an olefinic chain between glycosidic moieties is described. Cross metathesis reaction of 3' or 5' O-allyl analogues of thymidine led to the expected 3'-3' and 5'-5' dimeric compounds, respectively. In order to obtain the 3'-5' dimer, 5'-O-allyl and 3'-O-allyl monomers were first linked by their free 3' OH and 5' OH groups through a glutaryl spacer; ring closing metathesis was then operated upon this temporary dimer, followed by glutaryl removal.