N²-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(triisopropylsilyl)guanosine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) | 136044-37-6

• 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: N²-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(triisopropylsilyl)guanosine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
• 英文别名: N-[9-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxy-3-tri(propan-2-yl)silyloxyoxolan-2-yl]-6-oxo-1H-purin-2-yl]benzamide
• CAS: 136044-37-6
• 化学式: C₅₆H₇₂N₇O₉PSi
• 分子量: 1046.29
• InChiKey: MXJZDFNJKSDYFH-ARRNZZDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.52
• 重原子数：
  74
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  180
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N²-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(triisopropylsilyl)guanosine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以54%的产率得到N²-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(triisopropylsilyl)guanosine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  New nucleoside phosphoramidites and coupling protocols for solid-phase RNA synthesis

  摘要：

  The 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diethylphosphoramidites) 3, 5, 7, and 9, modified monomers for RNA synthesis, were prepared from 2-cyanoethyl N,N-diethylchloro-phosphoramidite (1). In conjunction with newly developed coupling protocols for automated solid-phase synthesis, they afforded synthetic oligoribonucleotides up to 74 base units in length. The performance of the new compounds was compared to the analogous 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) 4, 6, 8, and 10. Complete removal of benzoyl groups from N2-benzoylguanosine, which was incorporated into some of the synthetic oligoribonucleotides, was demonstrated. Purification procedures by reverse phase HPLC and PAGE methods are also presented.

  DOI：

  10.1021/jo00015a010

文献信息

• LYTTLE, MATTHEW H.;WRIGHT, PETER B.;SINHA, NANDA D.;BAIN, J. D.;CHAMBERLI+, J. ORG. CHEM., 56,(1991) N5, C. 4608-4615
  作者：LYTTLE, MATTHEW H.、WRIGHT, PETER B.、SINHA, NANDA D.、BAIN, J. D.、CHAMBERLI+

  DOI：——

  日期：——