1-(5'-deoxy-N⁶,N⁶-dibenzoyl-2',3'-O-isopropylidene adenosin-5'-yl)-2-methyl-3-phenylsulfonyl-isothiourea | 162757-18-8

• 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: 1-(5'-deoxy-N⁶,N⁶-dibenzoyl-2',3'-O-isopropylidene adenosin-5'-yl)-2-methyl-3-phenylsulfonyl-isothiourea
• 英文别名: methyl N'-[[(3aR,4R,6R,6aR)-4-[6-(dibenzoylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-N-(benzenesulfonyl)carbamimidothioate
• CAS: 162757-18-8
• 化学式: C₃₅H₃₃N₇O₇S₂
• 分子量: 727.822
• InChiKey: CZUXLPTXXNRBHO-IXXGIDSLSA-N

物化性质

• 沸点：
  894.8±75.0 °C(predicted)
• 密度：
  1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  51.0
• 可旋转键数：
  8.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  167.2
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-(5'-deoxy-N⁶,N⁶-dibenzoyl-2',3'-O-isopropylidene adenosin-5'-yl)-2-methyl-3-phenylsulfonyl-isothiourea 在 C₂⁽²⁾HF₃O₃ 作用下， 以 水 为溶剂， 反应 0.67h， 以71%的产率得到1-(N6-benzoyl-5'-deoxy-adenosin-5'-yl)-2-methyl-3-phenylsulfonyl-isothiourea
  参考文献：
  名称：

  Synthesis of an Uncharged cAMP-Analogue

  摘要：

  3'-O,5'-N-(N-phenylsulfonyliminocarbonyl)-5'-amino-5'-deoxy adenosine, an uncharged cAMP-analogue was synthesized. This was accomplished by treatment of 5'amino-5'-deoxy-2',3'-O-isopropylidene adenosine with dimethyl N-phenylsulfonyldithiocarbamate. After removal of the isopropylidene protecting group and treatment of the intermediate with benzoyl chloride, cyclisation was carried out in DMF containing 10 equivalents of potassium tert-butoxide. Final deprotection of the adenine moiety was carried out with hydrazine hydrate.

  DOI：

  10.1080/15257779508014657
• 作为产物：
  描述：

  5-氨基-5-脱氧-2,3-O-(1-甲基亚乙基)-腺苷酸 在 吡啶 作用下， 以 吡啶 为溶剂， 反应 6.0h， 生成 1-(5'-deoxy-N⁶,N⁶-dibenzoyl-2',3'-O-isopropylidene adenosin-5'-yl)-2-methyl-3-phenylsulfonyl-isothiourea
  参考文献：
  名称：

  Synthesis of an Uncharged cAMP-Analogue

  摘要：

  3'-O,5'-N-(N-phenylsulfonyliminocarbonyl)-5'-amino-5'-deoxy adenosine, an uncharged cAMP-analogue was synthesized. This was accomplished by treatment of 5'amino-5'-deoxy-2',3'-O-isopropylidene adenosine with dimethyl N-phenylsulfonyldithiocarbamate. After removal of the isopropylidene protecting group and treatment of the intermediate with benzoyl chloride, cyclisation was carried out in DMF containing 10 equivalents of potassium tert-butoxide. Final deprotection of the adenine moiety was carried out with hydrazine hydrate.

  DOI：

  10.1080/15257779508014657