3',5'-di-O-acetyl-N⁶-benzoyl-2'-deoxyadenosine | 30784-65-7

• 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: 3',5'-di-O-acetyl-N⁶-benzoyl-2'-deoxyadenosine
• 英文别名: N6-Benzoyl-3'-O, 5'-O-diacetyl-2'-deoxyadenosine；[(2R,3S,5R)-3-acetyloxy-5-(6-benzamidopurin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 30784-65-7
• 化学式: C₂₁H₂₁N₅O₆
• 分子量: 439.428
• InChiKey: OLKFCGIKFMQQMX-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  苯甲酰胺 、 9-(3,5-di-O-acetyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-bromopurine 在 tris(dibenzylideneacetone)dipalladium ⁽⁰⁾ chloroform adduct 1,1'-双(二苯基膦)二茂铁 、 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以66%的产率得到3',5'-di-O-acetyl-N⁶-benzoyl-2'-deoxyadenosine
  参考文献：
  名称：

  A Direct, Efficient Method for the Preparation of N⁶-Protected ¹⁵N-Labeled Adenosines

  摘要：

  N-6-Protected adenosines have been prepared from inosines by activation of the C6 position and Pd-catalyzed coupling with amides. An efficient route to [6-(NH2)-N-15]-N-6-benzoyladenosine and [1-N-15,6-(NH2)-N-15]-N-6-benzoyladenosine has been achieved.

  DOI：

  10.1021/jo049490u

文献信息

• Condensation of 1-Fluorofuranoses and Silylated Nucleobases Catalyzed by Tetrafluorosilane
  作者：Ryoji Noyori、Masahiko Hayashi

  DOI：10.1246/cl.1987.57

  日期：1987.1.5

  The title reaction provides a generally useful tool for nucleoside synthesis. The stereoselectivities are highly influenced by the fluoride substrates, and steric course of the reaction of O-benzylated ribofuranosyl fluoride is solvent dependent.

  标题反应为核苷合成提供了一个普遍有用的工具。立体选择性受氟化物底物的影响很大，并且 O-苄基化呋喃核糖基氟反应的空间过程是溶剂依赖性的。
• TRANSPROTECTION OF SILYL ETHERS OF NUCLEOSIDES IN FeCl₃ BASED IONIC LIQUIDS
  作者：Jitendra R. Harjani、Susheel J. Nara、Manikrao M. Salunkhe、Yogesh S. Sanghvi

  DOI：10.1081/ncn-200060305

  日期：2005.4.1

  Ionic liquid mediated deprotection of tert-butyldimethyl silyl (TBDMS) ethers derived from various primary and secondary alcohols have been studied and the reaction conditions optimized Deprotection of the silyl ethers in FeCl3 based ionic liquids in presence of acetic anhydride yielded the acetate esters of the corresponding alcohols in good yields. The transprotection methodology was extended to the silyl ethers Of nucleosides to yield the corresponding acetylated products.
• ADENOSINE DEAMINASE-STABLE ANTI-RETROVIRAL NUCLEOSIDES
  申请人：SCRIPPS CLINIC AND RESEARCH FOUNDATION

  公开号：EP0355135B1

  公开（公告）日：1993-08-04
• EP0355135A4
  申请人：——

  公开号：EP0355135A4

  公开（公告）日：1990-04-09
• US4997926A
  申请人：——

  公开号：US4997926A

  公开（公告）日：1991-03-05