N⁴-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxycytidine | 108554-86-5

• 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: N⁴-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxycytidine
• 英文别名: prop-2-enyl N-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• CAS: 108554-86-5
• 化学式: C₃₄H₃₅N₃O₈
• 分子量: 613.667
• InChiKey: SYCDVQYCMRFSNL-ILJQZKEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  45
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁴-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxycytidine 、 双(二乙胺)苯膦 在 四氮唑 、 二乙胺 作用下， 以 乙腈 为溶剂， 以66%的产率得到N⁴-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxycytidine 3'-(N,N-diethylphenylphosphonamidite)
  参考文献：
  名称：

  General Synthesis and Binding Affinity of Position-Selective Phosphonodiester- and Phosphotriester-Incorporated Oligodeoxyribonucleotides

  摘要：

  Synthesis of phosphonodiester- and phosphotriester-modified oligodeoxyribonucleotides has been accomplished via the phosphoramidite approach with allylic protection. The modification can be made at the selected position(s) of the oligomers. The efficiency of this method has been demonstrated by the synthesis of base-labile modified oligo(deoxyribonucleotide)s such as the methyl phosphates and phenylphosphonates. Melting temperatures of the duplexes containing these artificial strands indicate that the backbone-alternation, which is made at a single site, does not have a negative influence on the binding affinity to the complementary DNA.

  DOI：

  10.1021/jo00109a024
• 作为产物：
  描述：

  2'-脱氧胞苷盐酸盐 在 吡啶 、 碳酸氢钠 作用下， 反应 50.0h， 生成 N⁴-<(Allyloxy)carbonyl>-5'-O-(p,p'-dimethoxytrityl)-2'-deoxycytidine
  参考文献：
  名称：

  The allylic protection method in solid-phase oligonucleotide synthesis. An efficient preparation of solid-anchored DNA oligomers

  摘要：

  DOI：

  10.1021/ja00161a006

文献信息

• A general approach to nucleoside 3′- and 5′- monophosphates
  作者：Y. Hayakawa、S. Wakabayashi、T. Nobori、R. Noyori

  DOI：10.1016/s0040-4039(00)96095-7

  日期：1987.1

  Diallyloxyphosphorylation of nucleoside hydroxyls followed by palladium(0)-catalyzed deallylation provides a new, general method for the preparation of the 3′- and 5′-monophosphates.

  核苷羟基的二烯丙氧基磷酸化反应，再由钯（0）催化的脱醛反应，为制备3'-和5'-单磷酸酯提供了一种新的通用方法。
• Use of Allylic Protecting Groups for the Synthesis of Base-Sensitive Prooligonucleotides
  作者：Nicolas Spinelli、Albert Meyer、Yoshihiro Hayakawa、Jean-Louis Imbach、Jean-Jacques Vasseur

  DOI：10.1002/1099-0690(20021)2002:1<49::aid-ejoc49>3.0.co;2-7

  日期：2002.1
• XAYAKAVA, JOSIXIRO;TINO, YUKIESI;TAXARA, SINITIRO
  作者：XAYAKAVA, JOSIXIRO、TINO, YUKIESI、TAXARA, SINITIRO

  DOI：——

  日期：——
• HAYAKAWA, YOSHIHIRO;WAKABAYASHI, SHIGEHARU;NOYORI, RYOJI, 15TH SYMP. NUCL. ACIDS CHEM., SAPPORO, SEPT. 19TH - 21ST, 1988, OXFORD; W+
  作者：HAYAKAWA, YOSHIHIRO、WAKABAYASHI, SHIGEHARU、NOYORI, RYOJI

  DOI：——

  日期：——
• The allylic protection method in solid-phase oligonucleotide synthesis. An efficient preparation of solid-anchored DNA oligomers
  作者：Yoshihiro Hayakawa、Shigeharu Wakabayashi、Hisatoyo Kato、Ryoji Noyori

  DOI：10.1021/ja00161a006

  日期：1990.2