N-{7-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-ethoxymethyl]-6-oxo-6,7-dihydro-1H-purin-2-yl}-acetamide | 208758-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: N-{7-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-ethoxymethyl]-6-oxo-6,7-dihydro-1H-purin-2-yl}-acetamide
• CAS: 208758-60-5
• 化学式: C₂₇H₃₃N₅O₅Si
• 分子量: 535.675
• InChiKey: OTWXEHMEEDWBML-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  131.36
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-{7-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-ethoxymethyl]-6-oxo-6,7-dihydro-1H-purin-2-yl}-acetamide 在 吡啶 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 Diisopropyl-phosphoramidous acid (R)-2-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-ylmethoxy)-3-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-propyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Synthesis and Triplex Forming Properties of an Acyclic N⁷-Glycosylated Guanine Nucleoside

  摘要：

  A chiral acyclic nucleoside, one in which the ribose carbohydrate has been replaced with a glycerol-based linker, is prepared by glycosylating guanine at the N-7-nitrogen. The stereochemically pure derivative is converted to a DMT-protected phosphoramidite for incorporation into DNA sequences. Sequence containing the acyclic N-7-dG nucleoside are capable of forming DNA triplexes in which it is likely that the N-1-H and N-2-amino groups of the N-7-dG are involved in recognition of the guanine base in G-C base pairs.

  DOI：

  10.1080/07328319808003464
• 作为产物：
  描述：

  (2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-phenylmethoxypropan-2-ol 在 palladium dihydroxide 盐酸 、 N,O-双三甲硅基乙酰胺 、 四丁基碘化铵 、 环己烯 作用下， 反应 24.5h， 生成 N-{7-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-ethoxymethyl]-6-oxo-6,7-dihydro-1H-purin-2-yl}-acetamide
  参考文献：
  名称：

  Synthesis and Triplex Forming Properties of an Acyclic N⁷-Glycosylated Guanine Nucleoside

  摘要：

  A chiral acyclic nucleoside, one in which the ribose carbohydrate has been replaced with a glycerol-based linker, is prepared by glycosylating guanine at the N-7-nitrogen. The stereochemically pure derivative is converted to a DMT-protected phosphoramidite for incorporation into DNA sequences. Sequence containing the acyclic N-7-dG nucleoside are capable of forming DNA triplexes in which it is likely that the N-1-H and N-2-amino groups of the N-7-dG are involved in recognition of the guanine base in G-C base pairs.

  DOI：

  10.1080/07328319808003464