1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine | 906482-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine
• 英文别名: 1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxy-5-[(2-nitrophenyl)methoxy]oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 906482-24-4
• 化学式: C₃₈H₃₇N₃O₁₀
• 分子量: 695.726
• InChiKey: BEONLIMXMAFBIB-YTFBDJPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  51
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-4-o-nitrobenzyloxy-β-D-ribofuranosyl]thymine 、 双(二异丙基氨基)(2-氰基乙氧基)膦 在 四氮唑 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以98%的产率得到1-[2-deoxy-3-O-(N,N-diisopropyl-β-cyanoethylphosphoramidyl)-5-O-(4,4'-dimethoxytrityl)-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
• 作为产物：
  描述：

  1-(3-O-tert-butyldimethylsilyl-2,5-dideoxy-β-D-glycero-pent-4-enofuranosyl)thymine 在 吡啶 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-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.