chloro-(2-cyanoethyl)-diisopropylaminophosphane | 132133-40-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: chloro-(2-cyanoethyl)-diisopropylaminophosphane
• 英文别名: 2-cyanoethyl N,N-diisopropylchlorophosphoramidite；chloro-2-cyanoethyl-(N,N-dii-propylamino) phosphine；3-[chloro-[di(propan-2-yl)amino]phosphanyl]propanenitrile
• CAS: 132133-40-5
• 化学式: C₉H₁₈ClN₂P
• 分子量: 220.682
• InChiKey: MNZDCOHDXOTQON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  chloro-(2-cyanoethyl)-diisopropylaminophosphane 、 1-[(2R,4S,5R)-5-[[[4-(16-heptacyclo[15.12.0.02,15.03,8.09,14.018,23.024,29]nonacosa-1(17),2(15),3,5,7,9,11,13,18,20,22,24,26,28-tetradecaenylmethyl)phenyl]-bis(4-methoxyphenyl)methoxy]methyl]-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione 在 N,N-二异丙基乙胺 作用下， 生成
  参考文献：
  名称：

  4-(17-tetrabenzo[a,c,g,i]fluorenylmethyl)-41′,4″-Dimethoxytrityl Chloride: A hydrophobic 5′-protecting group for the separation of synthetic oligonucleotides.

  摘要：

  A new highly hydrophobic 5'-hydroxyl protecting group (Tbf-DMTr) has been designed for the purification of synthetic oligonucleotides. Tbf-DMTr-oligonucleotides are strongly retained on RP-HPLC allowing a facile separation from truncated sequences. Subsequently the group can be removed in acidic conditions. The ultra-violet properties of Tbf-DMTr enable easy detection. The synthesis and purification of long oligonucleotides (> 100 mer) is envisaged.

  DOI：

  10.1016/s0040-4039(00)61618-0

文献信息

• Reversible diselenide cross-links are formed between oligonucleotides containing 2′-deoxy-6-selenoinosine
  作者：Christopher Liczner、Vincent Grenier、Christopher J. Wilds

  DOI：10.1016/j.tetlet.2017.11.044

  日期：2018.1

  e (d6SeI) and incorporated this modification into an oligonucleotide by solid-phase synthesis. During cleavage from the solid-support and deprotection, spontaneous dimerization of this oligonucleotide occurs via formation of a diselenide cross-link between the modified nucleobases. This cross-link can be readily reduced to restore the single-stranded oligonucleotide. UV thermal denaturation and circular

  我们已经合成并表征了2'-脱氧-6-硒代肌苷的亚磷酰胺衍生物（d 6Se I），并通过固相合成将该修饰结合到寡核苷酸中。在从固相支持物切割和脱保护期间，该寡核苷酸的自发二聚化是通过在修饰的核碱基之间形成二硒化物交联而发生的。该交联可以容易地还原以恢复单链寡核苷酸。d 6Se的双链体的紫外热变性和圆二色谱我对所有四个天然核苷碱基配对发现，相对于2'-脱氧肌苷，在稳定性和结构上存在微小差异。这种含硒的核碱基修饰可能可用于DNA纳米材料和X射线晶体学。
• Nucleosides and Nucleotides. 131. Synthesis and Properties of Oligonucleotides Containing 5-Formyl-2'-deoxyuridine.
  作者：Akira ONO、Tomoko OKAMOTO、Michiyo INADA、Hiroshi NARA、Akira MATSUDA

  DOI：10.1248/cpb.42.2231

  日期：——

  corresponding to 1 was not detected clearly by HPLC analysis of a nucleoside mixture obtained by complete hydrolysis of I-1. Therefore, the oligonucleotide I-1 was treated with cyanomethylene-triphenylphosphorane to give an oligonucleotide containing (E) and (Z)-5-(2-cyanovinyl)-2'- deoxyuridine, which was then hydrolyzed, and the newly generated nucleosides were detected by HPLC analysis. The Tm of

  将胸苷转化为5-甲酰基-2'-脱氧尿苷（1），将其掺入寡核苷酸5'd（GGAGA1CTCC）3'（I-1）和5'd（GCTGC1GCGAAAGCTG）3'（II-1）。为避免副反应和降解，必须使用新开发的保护基N，N-二-（3,5-二氯苯基）乙二胺保护1的甲酰基。在用于寡核苷酸的酶完全消化的条件下，化合物1是不稳定的，因此通过HPLC分析通过I-1的完全水解获得的核苷混合物，没有清楚地检测到对应于1的峰。因此，将寡核苷酸I-1用氰基亚甲基三苯基膦处理，得到含有（E）和（Z）-5-（2-氰基乙烯基）-2'-脱氧尿苷的寡核苷酸，然后将其水解，并通过HPLC分析检测新产生的核苷。在包含0.01 M磷酸钠（pH 7.0）的缓冲液中，自我互补寡核苷酸I-1（40°C）的Tm高于亲本寡核苷酸5'd（GGAGATCTCC）3'（31°C）的Tm。 ）和0.1 M NaCl。在模板引物系统[引物，5'd（
• Synthesis of <i>cis</i>- and <i>trans</i>-α-<scp>l</scp>-[4.3.0]Bicyclo-DNA Monomers for Antisense Technology: Methods for the Diastereoselective Formation of Bicyclic Nucleosides
  作者：Stephen Hanessian、Benjamin R. Schroeder、Bradley L. Merner、Bin Chen、Eric E. Swayze、Punit P. Seth

  DOI：10.1021/jo401166q

  日期：2013.9.20

  reaction to a carbohydrate system. In the case of analogue 13, where a trans-ring junction was desired, an intermolecular diastereoselective Grignard reaction followed by ring-closing metathesis was used. In order to set the desired stereochemistry at the C5′ positions of both nucleoside targets, a study of diastereoselective Lewis acid mediated allylation reactions on a common bicyclic aldehyde precursor

  两个α-升-核糖-构型的双环核酸修饰，由类似物表示12和13，其是位于C差向异构体3 '和C 5 '已使用基于碳水化合物的方法来构建双环核心结构合成。分子内1-脯氨酸介导的羟醛反应被用于产生类似物12的顺式构型的环连接，并且代表了这种古老的有机催化反应在碳水化合物体系中的罕见应用。在模拟的情况下13，其中一个反需要一个环状连接，使用分子间非对映选择性格氏反应，然后进行闭环复分解。为了将期望的立体化学设置在两个核苷靶的C 5 '位置，进行了对非对映选择性路易斯酸介导的对常见双环醛前体的烯丙基化反应的研究。类似物12被掺入寡核苷酸序列中，并且热变性实验表明，当与互补的DNA和RNA配对时，它是不稳定的。但是，该构建体相对于DNA寡核苷酸显示出核酸酶稳定性的显着改善。
• [EN] NEW PHOSPHORAMIDITE COMPOUNDS<br/>[FR] NOUVEAUX COMPOSES PHOSPHORAMIDITES
  申请人：POSTECH FOUNDATION

  公开号：WO2004063208A1

  公开（公告）日：2004-07-29

  Novel phosphoramidites having various functional groups can be advantageously used as new building blocks to synthesize various oligodeoxyribonucleotides which are useful for the development of a highly efficient diagnostic agent and the synthesis of new nano structural oligodeoxyribonucleotides.

  具有各种功能基团的新型磷酰胺酯可以优势地用作合成各种寡脱氧核苷酸的新建筑单元，这对于开发高效的诊断试剂和合成新的纳米结构寡脱氧核苷酸是有用的。
• Synthesis and Incorporation ofC(5?)-Ethynylated Uracil-Derived Phosphoramidites into RNA
  作者：Simon Eppacher、Markus Christen、Andrea Vasella

  DOI：10.1002/hlca.200490271

  日期：2004.12

  The D-allo- and L-talo-hept-6-ynofuranosyluracil-derived phosphoramidites 11A and 11T were prepared in 9–10% yield over eight steps from the previously described propargylic alcohols 1A and 1T, respectively. The corresponding nucleotides were incorporated into rU14 by standard solid-phase synthesis. While the duplex consisting of rU14 with one L-talo-hept-6-ynofuranosyluracil in the middle of the strand

  的D-异体和L- TALO庚-6- ynofuranosyluracil衍生磷酰胺11A和11T在9-10％的产率制备了超过八个步骤与前面描述的炔丙醇1A和1T分别。通过标准固相合成将相应的核苷酸掺入rU 14中。虽然双工由Ru的14与一个L-距骨-庚-6- ynofuranosyluracil在链和rA的中间14（我⋅ V）具有相同的熔点为双工RU中的参考14 ⋅rA 14（我⋅ II），其中一个D-双工异体以RU的中间-庚-6- ynofuranosyluracil 14和RA 14（我⋅ III）熔融1.5比基准双工°降低。双工我⋅ VI由Ru的14具有六个L-距骨分布在整个链和RA庚-6- ynofuranosyluracils 14显示的熔点为11比基准双工°降低。相应的双工我⋅ IV的Ru 14具有6 D-同种异体-庚-6- ynofuranosyluracils和RA图14显