ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]acetate | 197784-37-5

• 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: ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]acetate
• 英文别名: ethyl 2-[(2S,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]acetate
• CAS: 197784-37-5
• 化学式: C₃₀H₃₄O₇
• 分子量: 506.596
• InChiKey: YMRMUNPZRYDFFJ-HZFUHODCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]acetate 在 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 77.0h， 生成 [2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]-N-{2-[4,7,10-tris(2,2,2-trifluoroacetyl)-1,4,7,10-tetraazacyclododecan-1-yl]ethyl}acetamide
  参考文献：
  名称：

  The Zn²⁺Complex of 1,4,7,10-Tetraazacyclododecane as an Artificial Nucleobase

  摘要：

  {2-Deoxy-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-alpha-Derythro-pentofuranosyl -N-{2-[4, 7, 10-tris(2,2,2-trifluoroacetyl)-1,4, 7, 10-tetraazacyclododecan-1-yl] ethyl acetamide (I) was prepared and incorporated into a 2'-O-methyl oligoribonucleotide. The hybridization, of this oligonucleotide with complementary 2'-O-methyl oligoribonucleotides incorporating one to five uracil bases opposite to the azacrown structure was studied in the absence and presence of Zn2+ Introduction of Zn2+ moderately stabilized the duplex with U-bulged targets.

  DOI：

  10.1080/15257770.2011.583809
• 作为产物：
  描述：

  ethyl 2,3,4-trideoxy-D-ribo-hept-2-enoate 在 吡啶 、 4-二甲氨基吡啶 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 ethyl [2-deoxy-5-O-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]acetate
  参考文献：
  名称：

  C-Glycoside phosphoramidite building block for versatile functionalization of oligodeoxyribonucleotides

  摘要：

  从 "2-脱氧-D-核糖 "开始，通过六个步骤合成了一种手性非核苷磷酸酰胺结构单元 4。它以传统方式用于机器辅助寡核苷酸合成。寡核苷酸链组装完成后，硫酯键会被各种亲核剂（氢氧根离子、丙烷-1,3-二胺、胱胺素、组胺）裂解，从而产生在寡核苷酸链中间带有一个系基的寡核苷酸共轭物。

  DOI：

  10.1039/a703059b

文献信息

• Ethyl[2-Deoxy-5-<i>O</i>-(4,4′-dimethoxytrityl)-α- and β-D-<i>erythro</i>-Pentofuranosyl] Acetates as Versatile Intermediates in Nucleic Acid Chemistry
  作者：Jari Hovinen、Alex Azhayev、Harri Salo、Juhani Vilpo

  DOI：10.1080/07328319908044686

  日期：1999.6

  The title compounds (1a,b) were synthesized in three steps from 2-deoxy-D-ribose, and used in the preparation of oligonucleotide conjugates, branched oligonucleotides as well as homo-N-nucleosides.
• The Zn²⁺Complex of 1,4,7,10-Tetraazacyclododecane as an Artificial Nucleobase
  作者：Maarit Laine、Maria Aromaa、Pasi Virta、Tuomas Lönnberg、Päivi Poijärvi-Virta、Harri Lönnberg

  DOI：10.1080/15257770.2011.583809

  日期：2011.7

  2-Deoxy-3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5-O-(4,4'-dimethoxytrityl)-alpha-Derythro-pentofuranosyl -N-2-[4, 7, 10-tris(2,2,2-trifluoroacetyl)-1,4, 7, 10-tetraazacyclododecan-1-yl] ethyl acetamide (I) was prepared and incorporated into a 2'-O-methyl oligoribonucleotide. The hybridization, of this oligonucleotide with complementary 2'-O-methyl oligoribonucleotides incorporating one to five uracil bases opposite to the azacrown structure was studied in the absence and presence of Zn2+ Introduction of Zn2+ moderately stabilized the duplex with U-bulged targets.
• C-Glycoside phosphoramidite building block for versatile functionalization of oligodeoxyribonucleotides
  作者：Jari Hovinen、Harri Salo

  DOI：10.1039/a703059b

  日期：——

  A chiral non-nucleosidic phosphoramidite building block containing a thioester function in its structure, 4, is synthesized in six steps starting from ‘2-deoxy-D-ribose’. It is used in the machine-assisted oligonucleotide synthesis in a conventional manner. Upon completion of the oligonucleotide chain assembly the thioester bond is cleaved with various nucleophiles (hydroxide ion, propane-1,3-diamine, cystamine, histamine), resulting in oligonucleotide conjugates with a tether group in the middle of the oligonucleotide chain.

  从 "2-脱氧-D-核糖 "开始，通过六个步骤合成了一种手性非核苷磷酸酰胺结构单元 4。它以传统方式用于机器辅助寡核苷酸合成。寡核苷酸链组装完成后，硫酯键会被各种亲核剂（氢氧根离子、丙烷-1,3-二胺、胱胺素、组胺）裂解，从而产生在寡核苷酸链中间带有一个系基的寡核苷酸共轭物。