5'-O-(4,4'-dimehoxytrityl)-3'-O,4'-C-methyleneuridine | 195705-21-6

• 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: 5'-O-(4,4'-dimehoxytrityl)-3'-O,4'-C-methyleneuridine
• 英文别名: 1-[(1R,3R,4R,5S)-1-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-2,6-dioxabicyclo[3.2.0]heptan-3-yl]pyrimidine-2,4-dione
• CAS: 195705-21-6
• 化学式: C₃₁H₃₀N₂O₈
• 分子量: 558.588
• InChiKey: YRMUJMCSRNMRAP-JZGWFFLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimehoxytrityl)-3'-O,4'-C-methyleneuridine 在 三氯乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 3′-O,4′-C-methyleneuridine
  参考文献：
  名称：

  Synthesis and conformation of 3′-O,4′-C-methyleneribonucleosides, novel bicyclic nucleoside analogues for 2′,5′-linked oligonucleotide modification

  摘要：

  新型双环核苷类似物 3-O,4-C-亚甲基核苷 1 可以从尿苷出发方便地制备；通过 PM3 计算和 1 H NMR 研究，发现 1 的糖褶皱几乎呈 S 构象。

  DOI：

  10.1039/a704376g
• 作为产物：
  描述：

  Benzoic acid (1R,3R,4R,5S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2,6-dioxa-bicyclo[3.2.0]hept-1-ylmethyl ester 在 吡啶 、 甲醇 、 sodium methylate 作用下， 反应 0.17h， 生成 5'-O-(4,4'-dimehoxytrityl)-3'-O,4'-C-methyleneuridine
  参考文献：
  名称：

  DNA triplex structures are stabilized by the incorporation of 3′-endo blocked pyrimidine nucleosides in the hoogsteen strand

  摘要：

  A short route to pyrimidine locked nucleosides has been developed for their incorporation in tripler forming oligonucleotides (TFO). Compared to oligonucleotides built with standard nucleosides, the modified TFOs containing 3'-endo blocked residues formed, with their corresponding DNA duplexes, more stable triple helix systems, an effect which might be ascribed to the 3'-endo pucker of the modified nucleoside residues. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00434-0

文献信息

• Synthesis and conformation of 3′,4′-BNA monomers, 3′-O,4′-C-methyleneribonucleosides
  作者：Satoshi Obika、Ken-ichiro Morio、Daishu Nanbu、Yoshiyuki Hari、Hiromi Itoh、Takeshi Imanishi

  DOI：10.1016/s0040-4020(02)00227-2

  日期：2002.4

  In order to develop novel 2′,5′-linked oligonucleotide analogues aimed for antivirus reagents and antisense/antigene oligonucleotides, novel nucleoside analogues, 3′-O,4′-C-methyleneribonucleosides (3′,4′-BNA monomers) were synthesized via two synthetic routes. The first route starting from uridine utilized a regioselective ring-closure reaction of the 4′-C-(p-toluenesulfonyl)oxymethyluridine derivative

  为了开发新颖的2'，旨在用于防病毒试剂和反义/反基因寡核苷酸，新的核苷类似物，3'- 5'-连接的寡核苷酸类似物ø，4'- Ç -methyleneribonucleosides（3'，4'-BNA单体）为通过两种合成途径合成。从尿苷开始的第一条路线利用了4'- C-（对甲苯磺酰基）氧基甲基尿苷衍生物的区域选择性闭环反应。第二种途径涉及1,2,3-三-O-乙酰基-4- C-（对甲苯磺酰基）氧基甲基核呋喃糖衍生物与核碱基的偶联反应，然后形成环氧乙烷环，得到3'，4'-BNA单体带有所有四个核碱基。通过1 H NMR，X-射线晶体学和计算分析，3的糖起皱'，发现4'-BNA单体在S-构象（C被限制1' -外-C 2' -内型褶皱模式）。
• Probing the furanose conformation in the 2′–5′strand of isoDNA : RNA duplexes by freezing the nucleoside conformations
  作者：Namrata Erande、Anita D. Gunjal、Moneesha Fernandes、Vaijayanti A. Kumar

  DOI：10.1039/c0cc05402j

  日期：——

  Sugar conformations in the isoDNA strand of isoDNA : RNA duplexes are preferred S-type locked/frozen in contrast to N-type locked conformations preferred in DNA : RNA duplexes.

  异二聚体DNA链中的糖构象：与DNA-RNA双链中偏好的N型锁定构象相比，异二聚体DNA链中更倾向于S型锁定/冻结构象。
• Preparation and properties of 2′,5′-linked oligonucleotide analogues containing 3′-O,4′-C-methyleneribonucleosides
  作者：Satoshi Obika、Ken-ichiro Morio、Yoshiyuki Hari、Takeshi Imanishi

  DOI：10.1016/s0960-894x(99)00028-1

  日期：1999.2

  Bicyclic nucleoside analogues, 3'-O,4'-C-methyleneuridine and -5-methyluridine, were successfully incorporated into oligonucleotides via connection with 2',5'-phosphodiester linkage, and hybridization behavior and nuclease stability of the modified oligonucleotides were investigated.

  通过与2'，5'-磷酸二酯键连接成功地将双环核苷类似物3'-O，4'-C-亚甲基尿苷和-5-甲基尿苷掺入寡核苷酸中，并研究了修饰寡核苷酸的杂交行为和核酸酶稳定性。
• NOVEL NUCLEOTIDE ANALOGUES
  申请人：Imanishi, Takeshi

  公开号：EP0963997A1

  公开（公告）日：1999-12-15

  An oligonucleotide analog or an antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized, is provided. It is an oligo- or polynucleotide analog containing one or more monomer units being nucleotide analogs of the general formula: where B may be identical or different, and is a pyrimidine or purine nucleic acid base, or a derivative thereof.

  本发明提供了一种寡核苷酸类似物或反义分子，它在体内与酶的水解程度极低，具有较高的有义链结合能力，并且易于合成。 它是一种寡核苷酸或多核苷酸类似物，含有一个或多个单体单元，这些单体单元是通式如下的核苷酸类似物：其中 B 可以相同或不同，并且是嘧啶或嘌呤核酸碱基或其衍生物。
• US6043060A
  申请人：——

  公开号：US6043060A

  公开（公告）日：2000-03-28