(2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl P-(2-cyanoethyl)-N,N-diisopropylphosphonamidate | 725223-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl P-(2-cyanoethyl)-N,N-diisopropylphosphonamidate
• CAS: 725223-47-2
• 化学式: C₄₇H₅₂N₇O₇P
• 分子量: 857.946
• InChiKey: KGIHTMDXDDJMOV-AKWFTNRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.0
• 重原子数：
  62.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  162.95
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl P-(2-cyanoethyl)-N,N-diisopropylphosphonamidate 、 alkaline earth salt of/the/ methylsulfuric acid 生成
  参考文献：
  名称：

  H-膦硫代磷酸酯方法在固相支持物上合成寡核苷二硫代磷酸酯

  摘要：

  通过使用H-硫代磷酸酯方法在固相支持物上使用双（2,6-二甲基苯基）磷酰氯作为偶联剂有效合成了硫代二磷酸酯型短寡核苷酸，其中在H-硫代磷酸酯低聚物组装完成后使用元素硫促进了氧化，与标准的H-膦酸酯法相同。

  DOI：

  10.1016/j.tet.2006.09.024
• 作为产物：
  描述：

  5'-O-(4,4'-二甲氧基三苯基)-N6-苯甲酰基-2'-脱氧腺苷-3'-(2-氰乙基-N,N-二异丙基)亚磷酰胺 、 丙烯腈 以 乙腈 为溶剂， 生成 (2R,3S,5R)-5-(6-benzamido-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)tetrahydrofuran-3-yl P-(2-cyanoethyl)-N,N-diisopropylphosphonamidate
  参考文献：
  名称：

  Stereoselective Synthesis of Alkylphosphonates:  A Facile Rearrangement of Cyanoethyl-Protected Nucleoside Phosphoramidites

  摘要：

  Cyanoethyl-protected nucleoside phosphoramidites undergo a facile Michaelis-Arbuzov reaction upon addition of acrylonitrile to afford cyanoethyl phosphonates. This rearrangement is stereoselective at room temperature, but racemization is observed at high temperatures, indicating two different pathways. A plausible mechanism is proposed for this reaction.

  DOI：

  10.1021/op030035u

文献信息

• Linking the 3′ Ends of Oligonucleotide Duplexes with Cystine Disulfide Bridges
  作者：Vicente Marchán、Daniel Pulido、Enrique Pedroso、Anna Grandas

  DOI：10.1002/ejoc.200500567

  日期：2006.2

  Oligonucleotide duplexes with cystine disulfide 3′-3′ interstrand cross-links were synthesized. Stepwise solid-phase procedures, followed by basic deprotection under controlled conditions and air oxidation, afforded various disulfide-linked duplexes differing in the peptide and oligonucleotide composition and length. Some of these nucleopeptides form unimolecular duplexes in which peptide–minor-groove

  合成了具有二硫化胱氨酸 3'-3' 链间交联的寡核苷酸双链体。逐步固相程序，然后在受控条件下进行碱性脱保护和空气氧化，提供了不同的肽和寡核苷酸组成和长度不同的二硫键连接的双链体。这些核肽中的一些形成单分子双链体，其中建立了肽-小槽相互作用，而另一些可能会产生扩展的纳米结构。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Solution Stability and Degradation Pathway of Deoxyribonucleoside Phosphoramidites in Acetonitrile
  作者：Achim H. Krotz、Claus Rentel、Dennis Gorman、Phil Olsen、Hans J. Gaus、James V. McArdle、Anthony N. Scozzari

  DOI：10.1081/ncn-120039215

  日期：2004.12.31

  The impuritiy profiles of acetonitrile solutions of the four standard O-cyanoethyl-N,N-diisopropyl-phosphoramidites of 5'-O-dimethoxytrityl (DMT) protected deoxyribo-nucleosides (dG(ib), dA(bz), dC(bz), T) were analyzed by HPLC-MS. The solution stability of the phosphoramidites decreases in the order T, dC > dA > dG. After five weeks storage under inert gas atmosphere the amidite purity was reduced by 2% (T, dC), 6% (dA), and 39% (dG), respectively. The main degradation pathways involve hydrolysis, elimination of acrylonitrile and autocatalytic acrylonitrile-induced formation of cyanoethyl phosphonoamidates. Consequently, the rate of degradation is reduced by reducing the water concentration in solution with molecular sieves and by lowering the amidite concentration. Acid-catalyzed hydrolysis could also be reduced by addition of small amounts of base.