2'-O-(tert-butyldimethylsilyl)-5'-O-(4-methoxytrityl)uridine | 65109-15-1

• 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: 2'-O-(tert-butyldimethylsilyl)-5'-O-(4-methoxytrityl)uridine
• 英文别名: 1-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-4-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 65109-15-1
• 化学式: C₃₅H₄₂N₂O₇Si
• 分子量: 630.813
• InChiKey: SSAKQXURXOTTIZ-PYTKSMOKSA-N

物化性质

• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2'-O-(tert-butyldimethylsilyl)-5'-O-(4-methoxytrityl)uridine 在 水 、 碘 、 N-methyl-aniline; salt of/the/ trichloroacetic acid 作用下， 生成
  参考文献：
  名称：

  A new method for the synthesis of branched ribonucleotides

  摘要：

  DOI：

  10.1016/s0040-4039(00)95416-9
• 作为产物：
  描述：

  尿嘧啶核苷 在 咪唑 作用下， 以 吡啶 、 二甲基亚砜 为溶剂， 反应 40.0h， 生成 2'-O-(tert-butyldimethylsilyl)-5'-O-(4-methoxytrityl)uridine
  参考文献：
  名称：

  Flockerzi, Dieter; Silber, Gunter; Charubala, Ramamurthy, Liebigs Annalen der Chemie, 1981, # 9, p. 1568 - 1585

  摘要：

  DOI：

文献信息

• Cleavage of the Phosphodiester Bond of Uridylyl-(3′,5′)-8-Carboxymethylaminoadenosine by Hydronium, Hydroxide and Zinc(Ii) Ions: A Model Study Aimed at Elucidating the Potential of a Carboxylate Function as an Intramolecular Catalyst
  作者：Satu Mikkola、Mikko Oivanen、Kari Neuvonen、Suvi Piitari、Kaisa Ketomäki、Harri Lönnberg

  DOI：10.1080/15257770008045452

  日期：2000.10

  Uridylyl-(3',5')-8-carboxymethylaminoadenosine has been synthesised, and its transesterification to uridine 2',3'-cyclic phosphate in the presence and absence of Zn2+ ion has been studied. The results show that a carboxylate function in the vicinity of the phosphodiester bond accelerates the metal ion promoted cleavage but not the metal ion independent reaction. Under acidic conditions, the predominant

  合成了铀酰-（3'，5'）-8-羧甲基氨基腺苷，并且研究了在有和没有Zn2 +离子的情况下将其酯交换为尿苷2'，3'-环状磷酸酯。结果表明，磷酸二酯键附近的羧酸盐功能促进金属离子促进的裂解，但不促进金属离子非依赖性反应。在酸性条件下，主要反应是侧链的裂解，得到8-氨基衍生物。
• Ceric Ammonium Nitrate on Silica Gel for Efficient and Selective Removal of Trityl and Silyl Groups
  作者：Jih Ru Hwu、Moti L. Jain、Fu-Yuan Tsai、Shwu-Chen Tsay、Arumugham Balakumar、Gholam H. Hakimelahi

  DOI：10.1021/jo000024o

  日期：2000.8.1

  triisopropylsilyl group from a primary hydroxyl functionality in di- or trisilyl ethers of ribonucleosides. A comparative study of deprotection reactions by utilization of CAN alone or CAN-SiO2 indicates a remarkable increase in the rate of the reactions involving a solid support. The mechanism of electron-transfer processes is proposed for the use of CAN-SiO2 in the removal of these protective groups from organic

  发现硅胶负载的硝酸铈铵（CAN-SiO2）在温和条件下可从受保护的核苷和核苷酸中快速选择性地裂解三苯甲基（Tr），单甲氧基三苯甲基（MMTr）和二甲氧基三苯甲基（DMTr）基团。脱保护的效率取决于所得碳阳离子物质的稳定性：DMTr +> MMTr +> Tr +。使用催化量的这种固体负载的试剂还可以有效地和选择性地从核糖核苷的二或三甲硅烷基醚中的伯羟基官能团中除去叔丁基二甲基甲硅烷基或三异丙基甲硅烷基。通过单独使用CAN或CAN-SiO2进行脱保护反应的比较研究表明，涉及固相支持物的反应速率显着提高。
• Nucleotide. XV. Synthese und Eigenschaften von 2?-O-t-Butyldimethylsilyl-5?-O-monomethoxytritylribonucleosid-3?-phosphotriestern, Ausgangssubstanzen f�r Oligonucleotid-Synthesen
  作者：Gunter Silber、Dieter Flockerzi、Rajendra Singh Varma、Ramamurthy Charubala、Eugen Uhlmann、Wolfgang Pfleiderer

  DOI：10.1002/hlca.19810640548

  日期：1981.7.22

  Nucleotides. XV. Synthesis and Properties of 2′O-t-Butyldimethylsilyl-5′-O-monomethoxytritylribonucleoside-3′-phosphotriesters, Starting Materials for Oligonucleotide Syntheses

  核苷酸。XV。合成及2个属性“ Ø -牛逼丁基二甲硅烷-5' Ø -monomethoxytritylribonucleoside-3'磷酸三酯，起始材料合成寡核苷酸
• Formation of Interribonucleoside Phosphate Bond by the Use of Reagent Formed by the Reaction of 2-Chlorophenyl Phosphorodichloridate with 5-Nitrobenzotriazole and Preparation of Anticodon Triplet of Yeast tRNA^Lys
  作者：Hiroshi Seki、Oyo Mitsunobu

  DOI：10.1246/cl.1987.775

  日期：1987.5.5

  The reagent formed by the reaction of 2-chlorophenyl phosphorodichloridate with an equimolar amount of 5-nitrobenzotriazole was treated with protected ribonucleosides having free 3′-OH, followed by protected ribonucleosides having free 5′-OH in pyridine for 8 h (the second step), the corresponding dinucleoside phosphates being obtained in 55–84% yields. When the second step was carried out in the presence of 2,6-lutidine, the yields were increased to 80–90% within 2h. By this procedure, the anticodon triplet of yeast tRNALys was prepared in 71% yield.

  由2-氯苯基磷酸二氯酯与等摩尔量的5-硝基苯并三唑反应生成的试剂，经过处理带有游离3′-OH的保护核糖核苷，然后再处理带有游离5′-OH的保护核糖核苷，在吡啶中反应8小时（第二步），获得相应的二核苷酸磷酸盐，产率为55–84%。当第二步在2,6-路丁啶存在下进行时，产率在2小时内提高至80–90%。通过此步骤，酵母tRNALys的反密码子三联体以71%的产率制备成功。
• A CONVENIENT PROCEDURE FOR THE PREPARATION OF DINUCLEOSIDE PHOSPHATES By THE USE OF A BIFUNCTIONAL PHOSPHORYLATING REAGENTS, 2-CHLOROPHENYLPHOSPHOROBIS(NITROBENZOTRIAZOLIDE)
  作者：Oyo Mitsunobu、Miyako Takahashi、Hiroshi Seki、Makoto Arai、Fumiko Yasumoto、Hideaki Iwami、Naoto Kawakami、Junko Kamishiro

  DOI：10.1246/cl.1985.949

  日期：1985.7.5

  The reagent formed By the reaction of 2-chlorophenyl phosphorodichloridate with 2 molar amounts of 5-nitrobenzotriazole was allowed to react successively with nucleosides having free 3′-hydroxyl groups and nucleosides having free 5′-hydroxyl groups affording the corresponding dinucleoside phosphates in 63–97% yields.

  2-chlorophenyl phosphorodichloridate 与 2 摩尔量的 5-nitrobenzotriazole 反应生成的试剂先后与具有游离 3′-hydroxyl 基团的核苷和具有游离 5′-hydroxyl 基团的核苷反应，得到相应的二核苷磷酸酯，产率为 63-97%。