5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)uridine | 863408-40-6

• 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'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)uridine
• 英文别名: 5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)uridine；5′-O-DMTr-2′-O-CEM-uridine；3-[[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxymethoxy]propanenitrile
• CAS: 863408-40-6
• 化学式: C₃₄H₃₅N₃O₉
• 分子量: 629.667
• InChiKey: KORYEUNRGHBEFS-PYTKSMOKSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)uridine 在 二氯乙酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.69h， 生成
  参考文献：
  名称：

  Stereocontrolled Solid-Phase Synthesis of Phosphorothioate Oligoribonucleotides Using 2′-O-(2-Cyanoethoxymethyl)-nucleoside 3′-O-Oxazaphospholidine Monomers

  摘要：

  A method for the synthesis of P-stereodefined phosphorothioate oligoribonucleotides (PS-ORNs) was developed. PS-ORNs of mixed sequence (up to 12mers) were successfully synthesized by this method with sufficient coupling efficiency (94-99%) and diastereoselectivity (>= 98:2). The coupling efficiency was greatly improved by the use of 2-cyanoethoxymethyl (CEM) groups in place of the conventional TBS groups for the 2'-O-protection of nucleoside 3'-O-oxazaphospholidine monomers. The resultant diastereopure PS-ORNs allowed us to clearly demonstrate that an ORN containing an all-(Rp)-PS-backbone stabilizes its duplex with the complementary ORN, whereas its all-(Sp)-counterpart has a destabilizing effect.

  DOI：

  10.1021/jo301052v
• 作为产物：
  描述：

  尿嘧啶核苷 在 吡啶 、 二丁基二氯化锡 、 N,N-二异丙基乙胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 生成 5'-O-(4,4'-dimethoxytrityl)-2'-O-(2-cyanoethoxymethyl)uridine
  参考文献：
  名称：

  具有2'-O-（2-氰基乙氧基甲基）保护基的RNA合成新方法。

  摘要：

  已开发出一种新的合成方法，该方法以2-氰基乙氧基甲基（CEM）为2'-羟基保护基的RNA低聚物的合成。这种新方法可以合成寡核糖核苷酸，其效率和最终纯度可与DNA合成获得的效率和最终纯度相媲美。[结构：见文字]

  DOI：

  10.1021/ol051151f

文献信息

• Synthesis and properties of novel 2′-O-alkoxymethyl-modified nucleic acids
  作者：Koichiro Arai、Naoki Uchiyama、Takeshi Wada

  DOI：10.1016/j.bmcl.2011.09.003

  日期：2011.11

  Novel 2′-O-modified oligoribonucleotides with alkoxymethyl skeletons were synthesized, and their ability to hybridize complementary nucleic acids and their nuclease resistance were analyzed. The hybridization ability was improved by introducing electron-withdrawing groups and the increases in melting temperature (Tm value) was particularly high for chlorine-substituted compounds. Nuclease resistance

  合成了具有烷氧基甲基骨架的新型2'- O-修饰寡核苷酸，并分析了其互补核酸杂交的能力和核酸酶的抗性。通过引入吸电子基团提高了杂交能力，并且对于氯取代的化合物，熔融温度（T m值）的增加特别高。这些2'- O-烷氧基甲基化的低聚物的核酸酶抗性低于预期，但是氰基取代导致的核酸酶抗性高于2'- O-甲基化。
• METHOD FOR PREPARING RIBONUCLEOSIDE PHOSPHOROTHIOATE
  申请人：Wada Takeshi

  公开号：US20130184450A1

  公开（公告）日：2013-07-18

  A method for preparing a phosphorothioate RNA based on the oxazaphospholidine method, wherein cyanoethoxymethyl group is used instead of tert-butyldimethylsilyl group as a protective group of 2′-hydroxyl group of RNA.

  一种基于氧磷硫酸酯RNA的制备方法，其中使用氰乙氧甲基基团代替叔丁基二甲基硅基团作为RNA的2'-羟基的保护基。
• METHOD FOR DETACHING PROTECTING GROUP ON NUCLEIC ACID
  申请人：Shiba Yoshinobu

  公开号：US20090149645A1

  公开（公告）日：2009-06-11

  A method is provided for removing a 2-cyanoethoxymethyl (CEM) group and substituting the 2′-hydroxyl group of each ribose of an oligonucleic acid derivative with good reproducibility and high efficiency.

  提供了一种方法，用于去除2-氰乙氧甲基（CEM）基团，并将寡核苷酸衍生物的每个核糖的2'-羟基以良好的可重复性和高效率进行置换。
• Phosphoramidite Compound And Method For Producing Oligo-Rna
  申请人：Ohgi Tadaaki

  公开号：US20070282097A1

  公开（公告）日：2007-12-06

  An object of the present invention is to provide a useful and novel phosphoramidite compound for the synthesis of oligo-RNA. A phosphoramidite compound represented by general formula (1), wherein: B X represents a nucleobase optionally having a protecting group; and R 1 is a substituent represented by general formula (2), wherein: R 11 , R 12 and R 13 are the same or different and each represents hydrogen or alkoxy; R 2a and R 2b are the same or different and each represents alkyl, or R 2a and R 2b taken together with the adjacent nitrogen atom may form a 5- to 6-membered saturated amino cyclic group, the amino cyclic group optionally having an oxygen or sulfur atom as a ring-composing member in addition to the adjacent nitrogen atom; and WG 1 and WG 2 are the same or different and each represents an electron-withdrawing group.

  本发明的目的是提供一种用于合成寡聚核糖核酸的有用和新颖的磷酰胺酯化合物。一种由通式（1）表示的磷酰胺酯化合物，其中：BX代表一个核碱基，可选地具有保护基；而R1是由通式（2）表示的取代基，其中：R11、R12和R13相同或不同，每个代表氢或烷氧基；R2a和R2b相同或不同，每个代表烷基，或者R2a和R2b与相邻的氮原子一起可以形成5-至6-环饱和氨基环族，该氨基环族可选地具有一个氧或硫原子作为环成员，除了相邻的氮原子之外；而WG1和WG2相同或不同，每个代表一个电子吸引基团。
• METHOD FOR REMOVAL OF NUCLEIC ACID-PROTECTING GROUP
  申请人：Kitagawa Hidetoshi

  公开号：US20090312534A1

  公开（公告）日：2009-12-17

  A method is provided for efficiently removing the silicon substituent which protects the 3′-hydroxyl group and the 5′-hydroxyl group of a ribose of a ribonucleic acid derivative in which the 2′-hydroxyl group of the ribose is protected with the following substituent (I) where WG1 represents an electron withdrawing group, and the 3′-hydroxyl group and the 5′-hydroxyl group of the ribose are protected with a silyl protecting group.

  提供了一种高效去除硅代替基的方法，该硅代替基保护着核糖核酸衍生物的3'-羟基和5'-羟基，其中核糖的2'-羟基被以下代替基(I)保护，其中WG1代表电子吸引基团，并且核糖的3'-羟基和5'-羟基被硅保护基保护。