9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-bromo-1,9-dihydro-purin-6-one | 218431-16-4

• 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: 9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-bromo-1,9-dihydro-purin-6-one
• 英文别名: 9-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-8-bromo-1H-purin-6-one
• CAS: 218431-16-4
• 化学式: C₂₈H₅₃BrN₄O₅Si₃
• 分子量: 689.913
• InChiKey: LHWJWDLDJLXDTR-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.99
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  96.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-bromo-1,9-dihydro-purin-6-one 在 四(三苯基膦)钯 、 sodium methylate 、 sodium 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 、 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 44.0h， 生成 1-propyl-8-(2''-pyrrolyl)-9-[2',3',5'-tri-O-(tert-butyldimethylsilyl)-β-D-ribofuranosidyl]-purin-6-one
  参考文献：
  名称：

  Enhancing Hoogsteen Interactions:  A Pyrrole-Containing Purine Nucleoside That Competes with Guanosine Self-Assembly

  摘要：

  A pyrrole-appended purine nucleoside 1 is described that can form an "extended" three-point Hoogsteen-type interaction due to the stabilization of the donor-acceptor-acceptor (DAA) motif. Nucleoside 1 is shown to bind guanosine 10 (a classic ADD motif) to form ensemble I. This interaction competes effectively with guanosine self-assembly and, as such, is capable of disrupting guanosine quadruplex formation.

  DOI：

  10.1021/ja046773v
• 作为产物：
  描述：

  2',3',5'-tris-O-(tert-butyldimethylsilyl)inosine 在 溴化氰 、 lithium diisopropyl amide 作用下， 生成 9-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-8-bromo-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Nolsoe, Jens M. J.; Gundersen, Lise-Lotte; Rise, Frode, Synthetic Communications, 1998, vol. 28, # 23, p. 4303 - 4315

  摘要：

  DOI：

文献信息

• Enhancing Hoogsteen Interactions:  A Pyrrole-Containing Purine Nucleoside That Competes with Guanosine Self-Assembly
  作者：Jonathan L. Sessler、Janarthanan Jayawickramarajah、Courtney L. Sherman、Jennifer S. Brodbelt

  DOI：10.1021/ja046773v

  日期：2004.9.1

  A pyrrole-appended purine nucleoside 1 is described that can form an "extended" three-point Hoogsteen-type interaction due to the stabilization of the donor-acceptor-acceptor (DAA) motif. Nucleoside 1 is shown to bind guanosine 10 (a classic ADD motif) to form ensemble I. This interaction competes effectively with guanosine self-assembly and, as such, is capable of disrupting guanosine quadruplex formation.
• Nolsoe, Jens M. J.; Gundersen, Lise-Lotte; Rise, Frode, Synthetic Communications, 1998, vol. 28, # 23, p. 4303 - 4315
  作者：Nolsoe, Jens M. J.、Gundersen, Lise-Lotte、Rise, Frode

  DOI：——

  日期：——