1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-α-L-lyxofuranosyl]thymine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-α-L-lyxofuranosyl]thymine
• 英文别名: 1-[(2R,4S,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-(hydroxymethyl)-5-[(2-nitrophenyl)methoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₂₃H₃₃N₃O₈Si
• 分子量: 507.616
• InChiKey: BAXLWGPUYGWHRD-YYDVJCTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  邻硝基苯甲醇 、 1-(3-O-tert-butyldimethylsilyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine 在 间氯过氧苯甲酸 、 zinc chloride diethyl ether 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 以32%的产率得到1-[3-O-(t-butyldimethylsilyl)-2-deoxy-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine
  参考文献：
  名称：

  Photochemical Generation of C4‘-Oxidized Abasic Site Containing Oligodeoxynucleotide and Its Efficient Amine Modification

  摘要：

  We synthesized oligodeoxynucleotide (ODN, 3), which contains 4'-o-nitrobenzyloxythymidine (4) as a caged precursor of C4'-oxidized abasic site (1). Photoirradiation of 3 at 365 nm followed by amine treatment under neutral conditions afforded the lactam (2) efficiently. Duplexed ODN 3 was converted to 1 faster and more efficiently than single stranded 3, whereas amine treatment of 1 formed from single stranded 3 resulted in slightly faster lactam formation than with the duplex.

  DOI：

  10.1021/ol060987v

文献信息

• Photochemical Generation of C4‘-Oxidized Abasic Site Containing Oligodeoxynucleotide and Its Efficient Amine Modification
  作者：Mariko Aso、Kazuteru Usui、Mitsuhiro Fukuda、Yoshie Kakihara、Tsuyoshi Goromaru、Hiroshi Suemune

  DOI：10.1021/ol060987v

  日期：2006.7.1

  We synthesized oligodeoxynucleotide (ODN, 3), which contains 4'-o-nitrobenzyloxythymidine (4) as a caged precursor of C4'-oxidized abasic site (1). Photoirradiation of 3 at 365 nm followed by amine treatment under neutral conditions afforded the lactam (2) efficiently. Duplexed ODN 3 was converted to 1 faster and more efficiently than single stranded 3, whereas amine treatment of 1 formed from single stranded 3 resulted in slightly faster lactam formation than with the duplex.