2'-O-(4-methoxybenzyl)-N⁶-benzoyladenosine | 80015-58-3

• 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: 2'-O-(4-methoxybenzyl)-N⁶-benzoyladenosine
• 英文别名: N⁶-benzoyl-2'-O-(4-methoxybenzyl)adenosine；N⁶-benzoyl-2'-O-(p-methoxybenzyl)adenosine；6-N-benzoyl-2'-O-p-methoxybenzyladenosine；N-Benzoyl-2'-O-p-methoxybenzyladenosine；N-Benzoyl-2'-O-[(4-methoxyphenyl)methyl]adenosine；N-[9-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-[(4-methoxyphenyl)methoxy]oxolan-2-yl]purin-6-yl]benzamide
• CAS: 80015-58-3
• 化学式: C₂₅H₂₅N₅O₆
• 分子量: 491.503
• InChiKey: YTPKJFLYEINBGX-GUQHISFFSA-N

物化性质

• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2'-O-(4-methoxybenzyl)-N⁶-benzoyladenosine 在 吡啶 、 N-甲基咪唑 作用下， 反应 1.0h， 生成 Phosphoric acid (2R,3R,4R,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 5-chloro-quinolin-8-yl ester
  参考文献：
  名称：

  合成2 “ -或3 ” -O-（4-甲氧基苄基）核苷及其在应用3 '劳斯肉瘤病毒35S RNA合成的末端nonanucleotide序列

  摘要：

  通过用4-甲氧基-苯基重氮甲烷处理尿苷，N 4-苯甲酰基胞苷，N 6-苯甲酰基腺苷和N 2-苯甲酰基鸟苷来合成2'-或3'-O-（4-甲氧基苄基）核苷衍生物。通过使用N-酰化的核苷，可以在硅胶柱色谱上分离2'-或3'-异构体，并且这些化合物可用作通过磷酸三酯法合成寡核糖核苷酸的有用起始原料。通过快速方法合成了三聚体嵌段UU-Cp，AC-Cp和ACA。劳斯肉瘤病毒35S RNA的3'端九核苷酸UUCACCACA是通过三聚体的嵌段缩合获得的。

  DOI：

  10.1016/s0040-4020(01)82051-2
• 作为产物：
  描述：

  (2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)tetrahydrofuran-3-ol 在 吡啶 、 ammonium hydroxide 作用下， 以 吡啶 为溶剂， 反应 4.25h， 生成 2'-O-(4-methoxybenzyl)-N⁶-benzoyladenosine
  参考文献：
  名称：

  Preparation of Protected Ribonucleosides Suitable for Chemical Oligoribonucleotide Synthesis

  摘要：

  DOI：

  10.1055/s-1985-31198

文献信息

• SYNTHESIS OF OLIGORIBONUCLEOTIDES USING 4-METHOXYBENZYL GROUP AS A NEW PROTECTING GROUP OF THE 2′-HYDROXYL GROUP OF ADENOSINE
  作者：Hiroshi Takaku、Kazuo Kamaike

  DOI：10.1246/cl.1982.189

  日期：1982.2.5

  4-Methoxybenzyl group was introduced directly to the 2′-hydroxyl group from the reaction of adenosine with 4-methoxybenzyl bromide in the presence of sodium hydride. The 2′-O-(4-methoxybenzyl)adenosine can be successfully used in the synthesis of oligoribonucleotides via phosphotriester approach. The 4-methoxybenzyl group was removed rapidly from the oligoribonucleotides by triphenylmethyl fluoroborate

  4-甲氧基苄基在氢化钠存在下直接引入腺苷与4-甲氧基苄基溴反应的2'-羟基中。2'-O-(4-甲氧基苄基)腺苷可成功用于通过磷酸三酯法合成寡核糖核苷酸。4-甲氧基苄基通过氟硼酸三苯甲酯从寡核糖核苷酸中快速去除，并且完全解封闭的寡核糖核苷酸通过酶水解表征。
• Synthesis of 2′,3″,4″-trisphosphate-containing analogs of adenophostin A
  作者：Nicole C.R. van Straten、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4020(97)00308-6

  日期：1997.5

  Adenophostin A analog 4 was prepared via trimethylsilyl trifluoromethanesulfonate (TMSOTf)-assisted glycosylation of (S)-6-N-diphenylacetyl-9-(2-tert-butyldiphenylsilyloxy-1-hydroxyprop-3-yl)-adenine (11) with trichloroacetimidate donor 12 to give dimer 13. Protective group manipulations on 13 followed by phosphitylation with N,N-diisopropyl-bis-[2-(methylsulfonyl)ethyl] phosphoramidite (17) and in situ oxidation gave, after deprotection, (25)-9-1-(alpha-D-glucopyranosyloxy 3,4-bisphosphate)-2-monophosphate-prop-3-yl}-adenine (4) Condensation of phosphoryloxymethyladenosine 25 with D-arabinitol derivative 21 under the agency of TMSOTf afforded methylene acetal 26. Protective group manipulations (--> 32), phosphorylation, and deprotection yielded 3'-O-(D-arabinitol-4-O-methylene 2,3-bisphosphate)-adenosine 2'-monophosphate (5), a methylene acetal-containing analog of adenophostin A. (C) 1997 Elsevier Science Ltd.
• WO2020016782A5
  申请人：——

  公开号：WO2020016782A5

  公开（公告）日：2022-07-14
• Towards the preparation of 2″-deoxy-2″-fluoro-adenophostin A. Study of the glycosylation reaction
  作者：David Benito、M. Isabel Matheu、Alain Morère、Yolanda Díaz、Sergio Castillón

  DOI：10.1016/j.tet.2008.09.014

  日期：2008.11

  The synthesis of 2 ''-deoxy-2 ''-fluoro-adenophostin A framework starting from tri-O-acetylglucal and adenosine is described. The key steps are the formation of the 2-deoxy-2-fluoroglycosyl donor by electrophilic fluorination of tri-O-acetylglucal and the stereoselective glycosylation of a suitable adenosine derivative. The glycosylation reaction was optimized affording the desired 2 ''-deoxy-2 ''-fluoroglycoside with excellent alpha-stereoselectivity and in good yields, taking into account that glycosylations using nucleosides as glycosyl acceptors do not usually give excellent results. In that sense, an improvement of the glycosylation step with respect to that of the reported adenophostin synthesis, using adenosine derivatives as glycosyl donors, has been made. (C) 2008 Elsevier Ltd. All rights reserved.