N⁴-[(allyloxy)carbonyl]-2'-deoxycytidine | 102423-13-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-[(allyloxy)carbonyl]-2'-deoxycytidine
• 英文别名: prop-2-enyl N-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]carbamate
• CAS: 102423-13-2
• 化学式: C₁₃H₁₇N₃O₆
• 分子量: 311.294
• InChiKey: NLCNGARLVDKYKN-IQJOONFLSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  121
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N⁴-[(allyloxy)carbonyl]-2'-deoxycytidine 在 吡啶 、 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 N⁴-allyloxycarbonyl-3'-O-p,p'-dimethoxytrityl-2'-deoxycytidine
  参考文献：
  名称：

  一种通过亚磷酰胺保护的亚磷酰胺方法，在3'-末端带有磷酸酯的寡脱氧核糖核苷酸的新方法：碱基不稳定的核苷酸-氨基酸和-肽结合物的有效合成

  摘要：

  开发了一种新的通过烯丙基保护的亚磷酰胺法合成3'-端磷酸化DNA低聚物的新方法。此方法对于制备具有碱基不稳定结构的衍生物（例如oligoDNA-OPO（OH）OCH 2 CH（R）Z ）特别有用，其中Z是吸电子功能。例如，寡核苷酸-氨基酸偶联物，5' TGTCGACACCCAATT 3' -OPO（OH）OCH 2 CH（NH 2）COOH，和一个寡核苷酸-肽缀合物，5' TGTCGACACCCAATT 3' -OPO（OH）OCH 2 CH（已获得高纯度的NH 2 COOH。

  DOI：

  10.1016/s0040-4039(99)00748-0
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 N-甲基咪唑 、 甲醇 、 硫酸氢铵 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 N⁴-[(allyloxy)carbonyl]-2'-deoxycytidine
  参考文献：
  名称：

  A Convenient Way to N-Allyloxycarbonyl Protected Adenosine and Cytidine Derivatives

  摘要：

  开发了一种使用市售烯丙氧基羰基氯作为保护试剂，向腺嘧啶和胞嘧啶基上引入烯丙氧基羰基保护基的简便方法。

  DOI：

  10.1055/s-1998-1822

文献信息

• Inverse Phosphotriester DNA Synthesis Using Photochemically-Removable Dimethoxybenzoin Phosphate Protecting Groups
  作者：Michael C. Pirrung、Lara Fallon、David C. Lever、Steven W. Shuey

  DOI：10.1021/jo951593c

  日期：1996.1.1

  A method has been developed to prepare short DNA sequences using light to deprotect a nucleoside 3'-phosphotriester, generating a phosphodiester useful for coupling with a free 5'-OH-nucleotide. The dimethoxybenzoin group is used as the photochemically-removable protecting group for the 3'-phosphate. Cyanoethyl is most effective as the second protecting group on the phosphodiester. Because the method is directed at the preparation and use of the DNA sequences while still bound to the support, allyl and allyloxycarbonyl protecting groups are used for the nitrogenous bases since, based on the work of Hayakawa and Noyori, they can be removed without cleaving the DNA from the support. Two simple trinucleotides have been prepared in solution using this method. It has been demonstrated that the photochemical deprotection conditions do not lead to the formation of cyclobutane dimers from adjacent T residues.
• Improved Methods for the Preparation of 2′-Deoxyribonucleoside and Ribonucleoside 3′-Phosphoramidites with Allylic Protectors
  作者：Sophie B. Heidenhain、Yoshihiro Hayakawa

  DOI：10.1080/07328319908044842

  日期：1999.8

  Improved methods of preparing 2'-deoxyribonucleoside and ribonucleoside 3'-phosphoramidites with allylic protecting groups, which serve as useful building blocks, particularly for the synthesis of base-labile derivatives, are developed.
• 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
• A FACILE SYNTHESIS OF 5′-END SOLID-ANCHORED, 3′-END FREE OLIGODEOXYRIBONUCLEOTIDES VIA THE (5′ → 3′)-ELONGATED PHOSPHORAMIDITE STRATEGY
  作者：Akira Sakakura、Yoshihiro Hayakawa

  DOI：10.1081/ncn-100002082

  日期：2001.2.28

  It is demonstrated that not only N-2- but also O-6-protection of the guanine base is necessary for obtaining the oligodeoxyribonucleotides in high yields and at a high purity in the solid-phase synthesis via the (5 ' --> 3 ')-chain elongated phosphoramidite approach.
• EP0604552A4
  申请人：——

  公开号：EP0604552A4

  公开（公告）日：1993-08-02