O⁶-allyl-N²-[(allyloxy)carbonyl]-2'-deoxyguanosine | 158391-96-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: O⁶-allyl-N²-[(allyloxy)carbonyl]-2'-deoxyguanosine
• 英文别名: prop-2-enyl N-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-prop-2-enoxypurin-2-yl]carbamate
• CAS: 158391-96-9
• 化学式: C₁₇H₂₁N₅O₆
• 分子量: 391.384
• InChiKey: XXTGHUQLZAZHAA-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  141
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  O⁶-allyl-N²-[(allyloxy)carbonyl]-2'-deoxyguanosine 在 吡啶 、 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (6-Allyloxy-9-{(2R,4S,5R)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-[(4-methoxy-phenyl)-diphenyl-methoxy]-tetrahydro-furan-2-yl}-9H-purin-2-yl)-carbamic acid allyl ester
  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：

  3',5'-di-O-acetyl-2'-deoxyguanosine 在 sodium hydroxide 、 叔丁基氯化镁 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 为溶剂， 反应 8.0h， 生成 O⁶-allyl-N²-[(allyloxy)carbonyl]-2'-deoxyguanosine
  参考文献：
  名称：

  Improved Methods for the Preparation of 2′-Deoxyribonucleoside and Ribonucleoside 3′-Phosphoramidites with Allylic Protectors

  摘要：

  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.

  DOI：

  10.1080/07328319908044842

文献信息

• A novel approach to oligodeoxyribonucleotides bearing phosphoric acid esters at the 3′-terminals via the phosphoramidite method with allyl protection: An efficient synthesis of base-labile nucleotide-amino acid and -peptide conjugates
  作者：Akira Sakakura、Yoshihiro Hayakawa、Hitoshi Harada、Masaaki Hirose、Ryoji Noyori

  DOI：10.1016/s0040-4039(99)00748-0

  日期：1999.6

  A new method for synthesis of 3′-end-phosphorylated DNA oligomers via the phosphoramidite method with allyl protection has been developed. This method is particularly useful for the preparation of derivatives with base-labile structures such as oligoDNA-OPO(OH)OCH2CH(R)Z, in which Z is an electron-withdrawing function. For example, a oligonucleotide-amino acid conjugate, 5′TGTCGACACCCAATT3′-OPO(OH)OCH2CH(NH2)COOH

  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。
• 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.
• 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.