5'-amino-5'-deoxy-2'-O-methyl-5'-C-[(S)-methoxyethyl]thymidine | 1400908-51-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-amino-5'-deoxy-2'-O-methyl-5'-C-[(S)-methoxyethyl]thymidine
• 英文别名: 6-deoxy-L-talHeptf2Me5N7Me(a)-thymin-1-yl；1-[(2R,3R,4R,5R)-5-[(1S)-1-amino-3-methoxypropyl]-4-hydroxy-3-methoxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1400908-51-1
• 化学式: C₁₄H₂₃N₃O₆
• 分子量: 329.353
• InChiKey: MIVQRBHHTATZOB-ZZZDWPBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-[2-O-acetyl-5-azido-3-O-benzyl-5-C-[(S)-2-(tert-butyldiphenylsiloxy)ethyl]-5,6-dideoxy-β-D-ribofuranosyl]thymine 在 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 palladium(II) hydroxide 、 sodium hydride 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 30.0 ℃ 、138.0 kPa 条件下， 反应 24.25h， 生成 5'-amino-5'-deoxy-2'-O-methyl-5'-C-[(S)-methoxyethyl]thymidine
  参考文献：
  名称：

  Studies toward Oxyacetamide-Linked RNA Analogues: Synthesis and Conformation of a Modified Dinucleoside

  摘要：

  A new oxyacetamide-modified dinucleoside with 5'-(S) chirality, a hydrophobic 5'-C-(2-methoxyethyl) group, and a 2'-O-methyl group was synthesized from D-glucose. This dinucleoside showed a helical structure based on CD and NMR spectroscopy. The sugar puckering at the 5' and 3' ends were found to be 'S'- and 'N'-types, respectively. These results were substantiated by ab initio density functional theory.

  DOI：

  10.1055/s-0031-1289783

文献信息

• Studies toward Oxyacetamide-Linked RNA Analogues: Synthesis and Conformation of a Modified Dinucleoside
  作者：Dilip Dhavale、Amit Jabgunde、Sachin Yeole、Shrihari Sanap、Shridhar Gadre

  DOI：10.1055/s-0031-1289783

  日期：2012.7

  A new oxyacetamide-modified dinucleoside with 5'-(S) chirality, a hydrophobic 5'-C-(2-methoxyethyl) group, and a 2'-O-methyl group was synthesized from D-glucose. This dinucleoside showed a helical structure based on CD and NMR spectroscopy. The sugar puckering at the 5' and 3' ends were found to be 'S'- and 'N'-types, respectively. These results were substantiated by ab initio density functional theory.