5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N³-(p-methoxybenzyl)-5-bromouridine | 1429644-26-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N³-(p-methoxybenzyl)-5-bromouridine
• 英文别名: 1-[(3aR,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-bromo-3-[(4-methoxyphenyl)methyl]pyrimidine-2,4-dione
• CAS: 1429644-26-7
• 化学式: C₂₆H₃₇BrN₂O₇Si
• 分子量: 597.578
• InChiKey: PDCHOBQTTTUFIP-YYTDSSBASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  86.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium cyanide 、 5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N³-(p-methoxybenzyl)-5-bromouridine 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以47%的产率得到5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N³-(p-methoxybenzyl)-6-cyanouridine
  参考文献：
  名称：

  Synthesis of 6-Alkyluridines from 6-Cyanouridine via Zinc(II) Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents

  摘要：

  6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2'-deoxyuridine without the protection at the N-3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.

  DOI：

  10.1021/jo400364p
• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylidene-5-bromouridine 、 4-甲氧基氯苄 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以67%的产率得到5'-O-tert-butyldimethylsilyl-2',3'-O-isopropylidene-N³-(p-methoxybenzyl)-5-bromouridine
  参考文献：
  名称：

  Synthesis of 6-Alkyluridines from 6-Cyanouridine via Zinc(II) Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents

  摘要：

  6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2'-deoxyuridine without the protection at the N-3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.

  DOI：

  10.1021/jo400364p

文献信息

• Synthesis of 6-Alkyluridines from 6-Cyanouridine via Zinc(II) Chloride-Catalyzed Nucleophilic Substitution with Alkyl Grignard Reagents
  作者：Yu-Chiao Shih、Ya-Ying Yang、Chun-Chi Lin、Tun-Cheng Chien

  DOI：10.1021/jo400364p

  日期：2013.4.19

  6-Cyanouracil derivatives underwent a direct nucleophilic substitution reaction with alkyl Grignard reagents in the presence of zinc(II) chloride as a catalyst to form the corresponding 6-alkyluracils. This methodology is applicable to sugar-protected 6-cyanouridine and 6-cyano-2'-deoxyuridine without the protection at the N-3-imide and provides a facile and general access to versatile 6-alkyluracil and 6-alkyluridine derivatives.