8-bromo-5'-phthalimido-5'-deoxy-2',3'-O-bis(tert-butyldimethylsilyl)adenosine | 671792-91-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 8-bromo-5'-phthalimido-5'-deoxy-2',3'-O-bis(tert-butyldimethylsilyl)adenosine
• 英文别名: 8-bromo-5'-phthalimido-5'-deoxy-2',3'-bis(O-tert-butyldimethylsilyl)adenosine
• CAS: 671792-91-9
• 化学式: C₃₀H₄₃BrN₆O₅Si₂
• 分子量: 703.784
• InChiKey: SHFZTCKGIMAFGK-BMWKMAGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  134.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  8-bromo-5'-phthalimido-5'-deoxy-2',3'-O-bis(tert-butyldimethylsilyl)adenosine 在 sodium azide 、 乙二胺 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 20.5h， 生成 8-azido-5'-(2-hydroxyethylamino)-5'-deoxy-2',3'-bis(O-tert-butyldimethylsilyl)adenosine
  参考文献：
  名称：

  Efficient Synthesis of Azide-Bearing Cofactor Mimics

  摘要：

  8-Azido-5'-aziridino-5'-deoxyadenosine (6), a novel cofactor mimic, was synthesized in nine steps from commercially available 2',3'-isopropylideneadenosine in similar to4% overall yield. Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation of the 5' amino group with iodoethanol necessitated by the high degree of lability endowed by the aryl azide moiety. Aziridine 6 is envisioned as a useful biochemical tool by which to probe DNA and protein methylation patterns.

  DOI：

  10.1021/jo035485z
• 作为产物：
  描述：

  2-(((3aR,4R,6R,6aR)-6-(6-氨基-9H-嘌呤-9-基)-2,2-二甲基四氢呋喃并[3,4-d][1,3]二氧代-4-基)甲基)异吲哚啉-1,3-二酮 在 咪唑 、 溴 、 sodium acetate 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 8-bromo-5'-phthalimido-5'-deoxy-2',3'-O-bis(tert-butyldimethylsilyl)adenosine
  参考文献：
  名称：

  Efficient Synthesis of Azide-Bearing Cofactor Mimics

  摘要：

  8-Azido-5'-aziridino-5'-deoxyadenosine (6), a novel cofactor mimic, was synthesized in nine steps from commercially available 2',3'-isopropylideneadenosine in similar to4% overall yield. Crucial to this success was a very unorthodox phthalimide cleavage procedure, C8 azidation prior to aziridination and late stage alkylation of the 5' amino group with iodoethanol necessitated by the high degree of lability endowed by the aryl azide moiety. Aziridine 6 is envisioned as a useful biochemical tool by which to probe DNA and protein methylation patterns.

  DOI：

  10.1021/jo035485z

文献信息

• Synthesis of an Azide-Bearing <i>N</i>-Mustard Analogue of <i>S</i>-Adenosyl-<scp>l</scp>-methionine
  作者：Van Mai、Lindsay R. Comstock

  DOI：10.1021/jo2019637

  日期：2011.12.16

  an azide-bearing N-mustard S-adenosyl-l-methionine (SAM) analogue, 8-azido-5′-(diaminobutyric acid)-N-iodoethyl-5′-deoxyadenosine, has been accomplished in 10 steps from commercially available 2′,3′-isopropylidene adenosine. Critical to this success was executing C8 azidation prior to derivatizing the 5′-position of the ribose sugar and the late stage alkylation of the 5′ amino group with bromoethanol

  叠氮基N-芥子S-腺苷-1-蛋氨酸（SAM）类似物8-叠氮基5'-（二氨基丁酸）-N-碘乙基-5'-脱氧腺苷的合成已从10步完成市售的2'，3'-异亚丙基腺苷。取得成功的关键是在将核糖的5'-位置衍生化之前进行C 8叠氮化，以及用溴乙醇将5'氨基进行后期烷基化，这是芳基叠氮化物部分的反应性所必需的。带有叠氮化物的N-芥末被设想为一种有用的生化工具，通过它可以探测DNA和蛋白质甲基化模式。