6-N-benzoyl-9-(2,3-O-ethoxymethylidene-β-D-ribofuranosyl)adenine | 10280-24-7

• 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: 6-N-benzoyl-9-(2,3-O-ethoxymethylidene-β-D-ribofuranosyl)adenine
• 英文别名: 6-N-benzoyl-2',3'-O-ethoxymethylideneadenosine；2',3'-O-ethoxymethylene-N(6)-benzoyladenosine；2',3'-O-ethoxymethylidene-N-benzoyladenosine；2',3'-ethoxymethylidene-N-benzoyladenosine；2',3'-ethoxymethyliden-N-benzoyladenosine；N⁶-benzoyl-O^2'_,O3'-ethoxymethanediyl-adenosine；N-[9-[(3aR,4R,6R,6aR)-2-ethoxy-6-(hydroxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]purin-6-yl]benzamide
• CAS: 10280-24-7
• 化学式: C₂₀H₂₁N₅O₆
• 分子量: 427.417
• InChiKey: UGVPGGGZEWJYIQ-BHQCLFLGSA-N

物化性质

• 熔点：
  90-120 °C
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-N-benzoyl-9-(2,3-O-ethoxymethylidene-β-D-ribofuranosyl)adenine 在 2,6-二甲基吡啶 、 三甲基溴硅烷 、 二丁基二氯化锡 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 68.0h， 生成
  参考文献：
  名称：

  Activation of human RNase L by 2′- and 5′-O-methylphosphonate-modified oligoadenylates

  摘要：

  To determine the influence of internucleotide linkage and sugar ring conformation, and the role of 5'-terminal phosphate, on the activation of human RNase L, a series of 2'- and 5'-O-methylphosphonate-modified tetramers were synthesized from appropriate monomeric units and evaluated for their ability to activate human RNase L. Tetramers pAAApcX modified by ribo, arabino or xylo 5'-phosphonate unit p(c)X activated RNase L with efficiency comparable to that of natural activator. Moreover, incorporation of phosphonate linkages ensured the stability against cleavage by nucleases. The substitution of 5'-terminal phosphate for 5'-terminal phosphonate in tetramer p(c)XAAA afforded tetramers with excellent activation efficiency and with complete stability against cleavage by phosphomonoesterases. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.040
• 作为产物：
  描述：

  原甲酸三乙酯 、 N6-苯甲酰基腺苷 在 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-N-benzoyl-9-(2,3-O-ethoxymethylidene-β-D-ribofuranosyl)adenine
  参考文献：
  名称：

  Ribo-,Xylo-, andArabino-Configured Adenine-Based Nucleoside Phosphonates: Synthesis of Monomers for Solid-Phase Oligonucleotide Assembly

  摘要：

  Adenine-based, regioisomeric nucleoside phosphonates with ribo, xylo and arabino configuration were synthesized in the protected form suitable for the phosphotriester-like, solid-phase synthesis of oligonucleotides. Phosphonate moiety was protected by 4-methoxy-1-oxido-2-picolyl group and the furanose hydroxyl by the dimethoxytrityl group.

  DOI：

  10.1081/ncn-120022734

文献信息

• Synthesis of oligoribonucleotides with phosphonate-modified linkages
  作者：Ondřej Páv、Ivana Košiová、Ivan Barvík、Radek Pohl、Miloš Buděšínský、Ivan Rosenberg

  DOI：10.1039/c1ob05488k

  日期：——

  Solid phase synthesis of phosphonate-modified oligoribonucleotides using 2′-O-benzoyloxymethoxymethyl protected monomers is presented in both 3′→5′ and 5′→3′ directions. Hybridisation properties and enzymatic stability of oligoribonucleotides modified by regioisomeric 3′- and 5′-phosphonate linkages are evaluated. The introduction of the 5′-phosphonate units resulted in moderate destabilisation of

  固相合成膦酸酯修饰的寡核糖核苷酸 2′- O-苯甲酰氧基甲氧基甲基被保护的单体在3'→5'和5'→3'两个方向上均存在。区域异构体3'-和-修饰的寡核糖核苷酸的杂交特性和酶稳定性5'-膦酸酯链接被评估。的介绍5'-膦酸酯 单位导致RNA / RNA双链体的适度去稳定化（ΔT米 -1.8°C / mod。），而引入 3'-膦酸酯 单元导致双工的相当大的不稳定（ΔT米-5.7°C / mod。）。分子动力学模拟已被用来解释这种行为。在核糖核酸酶A，磷酸二酯酶I和磷酸二酯酶II的存在下，两种类型的膦酸酯键均显示出显着的抗性。
• A new synthetic method for 5'-triphosphoryl-adenylyl-(2'-5')-adenylyl-(2'-5')-adenosine (2-5A) and 2-5A core using 3'-O-tetrahydrofuranyl-adenosine derivatives.
  作者：Eiko Ohtsuka、Akio Yamane、Morio Ikehara

  DOI：10.1248/cpb.30.376

  日期：——

  2' or 3'-O-Tetrahydrofuranyl derivatives of ribonucleosides have been synthesized by treating 2, 3-dihydrofurane with bis tert-butyldi-methylsilyl N-protected nucleosides. Using 3'-O-tetrahydrofuranyl-N-benzoyladenosine as the starting meterial 5'-phosphoryladenylyl-(2'-5')-adenylyl-(2'-5')-adenosine was synthesized in a good yield and converted to the triphosphoryl derivative (2-5A). The 2'-5' linked triadenylate (2-5A core) was also prepared by the same phosphotriester method.

  通过将2,3-二氢呋喃与双叔丁基二甲基硅烷保护的N-保护核苷反应，合成了2'或3'-O-四氢呋喃基核苷衍生物。以3'-O-四氢呋喃基-N-苯甲酰腺苷为起始物质，高产率地合成了5'-磷酸腺苷酰-(2'-5')-腺苷酰-(2'-5')-腺苷，并将其转化为三磷酸衍生物（2-5A）。通过相同的磷酸三酯法，也制备了2'-5'连接的三腺苷酸（2-5A核心）。
• Studies on transfer ribonucleic acids and related compounds. XLIV. A large-scale synthesis of the anticodon heptanucleotide of formyl-methionine transfer ribonucleic acid by using 2'-O-tetrahydrofuranylnucleosides.
  作者：EIKO OHTSUKA、MITSURU OHKUBO、AKIO YAMANE、MORIO IKEHARA

  DOI：10.1248/cpb.31.1910

  日期：——

  2'-O-Tetrahydrofuranyl nucleosides were prepared by an improved procedure via 3', 5'-tetraisopropyldisiloxanylnucleosides. A large scale synthesis of the anticodon heptanucleotide C-U-C-A-U-A-A of E. coli formylmethionine tRNA was performed by the phosphotriester method involving condensation of oligonucleotides having 2'-O-tetrahydrofuranyl protecting groups.

  通过改进的3',5'-四异丙基二硅氧烷基核苷路线，制备了2'-O-四氢呋喃基核苷。采用磷酰三酯法，涉及具有2'-O-四氢呋喃保护基团的寡核苷酸的缩合反应，进行了大肠杆菌甲酰甲硫氨酰tRNA的反密码子七核苷酸C-U-C-A-U-A-A的大规模合成。
• Ohtsuka, Eiko; Yamane, Akio; Ikehara, Morio, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1534 - 1543
  作者：Ohtsuka, Eiko、Yamane, Akio、Ikehara, Morio

  DOI：——

  日期：——
• Pressova, Martina; Smrt, Jiri, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 2, p. 487 - 497
  作者：Pressova, Martina、Smrt, Jiri

  DOI：——

  日期：——