6-(2,2-dibromovinyl)spongouridine | 245671-31-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 6-(2,2-dibromovinyl)spongouridine
• CAS: 245671-31-2
• 化学式: C₁₁H₁₂Br₂N₂O₆
• 分子量: 428.034
• InChiKey: IAQKOHQTOFVLLR-STRWAFKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.76
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  124.78
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-(2,2-dibromovinyl)spongouridine 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 3',5'-bis-O-(tert-butyldimethylsilyl)-6,1'-ethanospongouridine
  参考文献：
  名称：

  1,5-Translocation Strategy for Nucleoside Anomeric Radicals

  摘要：

  A new method for generating nucleoside anomeric radicals utilizing radical 1,5-translocation was developed. Two kinds of beta-halogenovinyl groups at the C6-position of uracil nucleosides were found to be a good radical source, which subsequently forms a nucleoside anomeric radical. The following 5-endo-trig cyclization gave anomeric spiro nucleosides as products.

  DOI：

  10.1080/07328319708006197
• 作为产物：
  描述：

  4-ethoxy-1-(β-D-arabinofuranosyl)-2(1H)-pyrimidinone 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 6-(2,2-dibromovinyl)spongouridine
  参考文献：
  名称：

  1,5-Translocation Strategy for Nucleoside Anomeric Radicals

  摘要：

  A new method for generating nucleoside anomeric radicals utilizing radical 1,5-translocation was developed. Two kinds of beta-halogenovinyl groups at the C6-position of uracil nucleosides were found to be a good radical source, which subsequently forms a nucleoside anomeric radical. The following 5-endo-trig cyclization gave anomeric spiro nucleosides as products.

  DOI：

  10.1080/07328319708006197

文献信息

• Cyclization Reactions of Nucleoside Anomeric Radical with Olefin Tethered on Base:  Factors That Induce Anomeric Stereochemistry
  作者：Atsushi Kittaka、Takashi Asakura、Tetsuya Kuze、Hiromichi Tanaka、Naoki Yamada、Kazuo T. Nakamura、Tadashi Miyasaka

  DOI：10.1021/jo990611d

  日期：1999.9.1

  Nucleoside anomeric radicals were formed through 1,5-translocation of vinyl radicals generated from the 2,2-dibromovinyl group tethered at the uracil 6-position (1, 2, and 4) by tin radical. The anomeric radicals attacked the resulting C-6 vinyl group in a 5-endo-trig manner to afford anomeric spiro nucleosides (11-13, 21, 23, and 24) with the 6,1'-etheno bridge as the major cyclized products. The anomeric stereochemistry of the cyclization was found to be affected by the 2'-substituent. To consider the structure of the intermediate anomeric radical, the reaction using alpha-6-(2,2-dibromovinyl)-2'-deoxyuridine 9 was investigated. The same anomeric beta/alpha-stereoselectivity as the counterpart of 2 showed that the nucleoside anomeric radical would have nearly a planar structure and the C1'-N1. bond rotation in the radical is much faster than cyclization. The origin of the minor spiro nucleosides (14-20, 22, and 25-28) with the 6,1'-ethano bridge has also been investigated and appeared to be (E)-6-(2-bromovinyl)uridine 7E, a reduced form of 1a, but not (Z)-6-(2-bromovinyl)uridine 7Z, which gave a novel type of unstable compound with 6-exomethylene structure 29 through a different reaction pathway. 6-Chloro-8-(2,2-dibromovinyl)purine nucleoside 10 was next studied, and not only 1,5- but also 1,6-translocated products were isolated.