N6,N6-dibenzoyl-9-[2-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-β-D-ribofuranosyl]adenine | 1306597-65-8

• 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: N6,N6-dibenzoyl-9-[2-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-β-D-ribofuranosyl]adenine
• 英文别名: N-[9-[(2R,3R,4R,5R)-3-[(2R,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]benzamide
• CAS: 1306597-65-8
• 化学式: C₄₃H₄₃N₅O₉
• 分子量: 773.843
• InChiKey: OSCYRGAJWHHNMV-AECLVKOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  169
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  N6,N6-dibenzoyl-9-[3,5-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-β-D-ribofuranosyl]adenine 在 甲胺 、 四丁基氟化铵 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 四氢呋喃 为溶剂， 反应 3.5h， 以69%的产率得到N6,N6-dibenzoyl-9-[2-O-(2,3,5-tri-O-benzyl-α-D-ribofuranosyl)-β-D-ribofuranosyl]adenine
  参考文献：
  名称：

  Ribosylation of Adenosine: An Orthogonally Protected Building Block for the Synthesis of ADP-Ribosyl Oligomers

  摘要：

  A method to ribosylate adenosine on the 2' hydroxyl function in an alpha-selective fashion and in good yield is presented. Protective groups chosen for the acceptor and donor used in this glycosylation not only direct alpha-selectivity but also allow the construction of a fully orthogonally protected building block for the future assembly of oligo-ADP-ribosylated peptides and proteins.

  DOI：

  10.1021/ol200971z

文献信息

• Ribosylation of Adenosine: An Orthogonally Protected Building Block for the Synthesis of ADP-Ribosyl Oligomers
  作者：Gerbrand J. van der Heden van Noort、Herman S. Overkleeft、Gijsbert A. van der Marel、Dmitri V. Filippov

  DOI：10.1021/ol200971z

  日期：2011.6.3

  A method to ribosylate adenosine on the 2' hydroxyl function in an alpha-selective fashion and in good yield is presented. Protective groups chosen for the acceptor and donor used in this glycosylation not only direct alpha-selectivity but also allow the construction of a fully orthogonally protected building block for the future assembly of oligo-ADP-ribosylated peptides and proteins.