N⁶,N⁶-dibenzoyl-5'-O-mesyl-2',3'-O-isopropylidene adenosine | 40982-79-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶,N⁶-dibenzoyl-5'-O-mesyl-2',3'-O-isopropylidene adenosine
• 英文别名: O-isopropylidene-2',3' N,N'-dibenzoyl-6 O-mesyl-5' adenosine；N⁶,N⁶-dibenzoyl-O^{2'_,O3'_{-isopropylidene-O}5'}-methanesulfonyl-adenosine；[(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 methanesulfonate
• CAS: 40982-79-4
• 化学式: C₂₈H₂₇N₅O₈S
• 分子量: 593.617
• InChiKey: XLXNZFIPQBLWJH-BMWKMAGWSA-N

物化性质

• 沸点：
  812.2±75.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  42.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  152.04
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  N⁶,N⁶-dibenzoyl-5'-O-mesyl-2',3'-O-isopropylidene adenosine 在 palladium on activated charcoal 甲醇 、 sodium azide 、 乙醇 、 氨 、 氢气 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~80.0 ℃ 、310.27 kPa 条件下， 反应 91.5h， 生成 5-氨基-5-脱氧-2,3-O-(1-甲基亚乙基)-腺苷酸
  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：

  腺苷 在 吡啶 作用下， 反应 2.0h， 生成 N⁶,N⁶-dibenzoyl-5'-O-mesyl-2',3'-O-isopropylidene adenosine
  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

文献信息

• Synthesis of 5′,8-cyclopurine and of 5′,6-cyclodihydropyrimidine nucleosides using intramolecular radical cyclisation based on the aryl telluride radical exchange process.
  作者：Derek H.R. Barton、Stephane D. Géro、Quiclet-Sire Béatrice、Mohammad Samadi、Claire Vincent

  DOI：10.1016/s0040-4020(01)80885-1

  日期：1991.11

  C-cyclopurine and C-cyclodihydropyrimidine nucleosides has been effected using 5′-aryltelluronucleosides. Generation of methyl radicals from the photolysis of the acetyl derivative of N-hydroxy-2-thiopyridone permitted, by radical exchange, the formation of 5′-nucleoside radicals which cyclized in satisfactory yields.

  C-环嘌呤和C-环二氢嘧啶核苷的合成已使用5'-芳基tellurourosidesides进行。通过N-羟基-2-硫代吡啶酮的乙酰基衍生物的光解反应生成甲基自由基，可以通过自由基交换形成5'-核苷自由基，并以令人满意的产率进行环化。
• Synthese de la cyclo-5'-8 desoxy-5' adenosine: stereochimie et mecanisme de la cyclisation d'un derive de l'iodo-5' adenosine par le zinc
  作者：J. Zylber、R. Pontikis、A. Merrien、C. Merienne、M. Baran-Marszak、A. Gaudemer

  DOI：10.1016/s0040-4020(01)83125-2

  日期：1980.1