3'-TBDPS-5'-p-Tol-thymidine | 197719-60-1

• 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: 3'-TBDPS-5'-p-Tol-thymidine
• 英文别名: TBDPS(-3)[Bz(4-Me)(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl；[(2R,3S,5R)-3-[tert-butyl(diphenyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 197719-60-1
• 化学式: C₃₄H₃₈N₂O₆Si
• 分子量: 598.771
• InChiKey: DHEPRDRWNQKQKG-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-TBDPS-5'-p-Tol-thymidine 在 硫酸氢铵 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 1,4-脱水-2-脱氧-3-O-[(叔丁基)二苯基硅]-D-赤式-戊-1-烯糖醇
  参考文献：
  名称：

  Facile Preparation of Protected Furanoid Glycals from Thymidine

  摘要：

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.

  DOI：

  10.1021/jo970947s
• 作为产物：
  描述：

  beta-胸苷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3'-TBDPS-5'-p-Tol-thymidine
  参考文献：
  名称：

  Facile Preparation of Protected Furanoid Glycals from Thymidine

  摘要：

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.

  DOI：

  10.1021/jo970947s

文献信息

• Non-standard nucleobases implementing the isocytidine and isoguanosine hydrogen bonding patterns
  申请人：——

  公开号：US07741294B1

  公开（公告）日：2010-06-22

  This invention provides compositions of matter that, when incorporated into an oligonucleotide, present to a complementary strand in a Watson-Crick pairing geometry a pattern of hydrogen bonds that is different from the pattern presented by adenine, guanine, cytosine, and thymine. Most specifically, this invention discloses and claims compositions of matter that present the same hydrogen bonding patterns as the isocytidine and isoguanosine nucleobases, but do not have unfavorable tautomeric forms, do not become disassociated from their sugar, and do not make major groove interactions, as much, as easily, or as strongly as isocytidine and isoguanosine.

  这项发明提供了物质组合，当纳入寡核苷酸时，向沃森-克里克配对几何结构中的互补链呈现一种氢键模式，该模式与腺嘌呤、鸟嘌呤、胞嘧啶和胸腺嘧啶呈现的模式不同。更具体地说，该发明揭示并声明了一种物质组合，其呈现与异胞嘧啶和异鸟嘌呤核碱基相同的氢键结合模式，但不具有不利的互变异构形式，不会从其糖中解离，并且不会像异胞嘧啶和异鸟嘌呤那样轻易地或强烈地进行主沟相互作用。
• Facile Preparation of Protected Furanoid Glycals from Thymidine
  作者：Melissa A. Cameron、Sarah B. Cush、Robert P. Hammer

  DOI：10.1021/jo970947s

  日期：1997.12.1

  The synthesis of O-silyl- and O-acyl-protected furanose glycals from free thymidine was investigated. The method of glycal formation reported by Pedersen et al. was successfully expanded to include 5-ester (toluoyl) protected glycals as well as various combinations of 5'-ester and 3- and 5-tert-butyldimethylsilyl and tert-butyldiphenylsilyl protection. Gram quantities of furanoid glycals can be prepared in a few days in two-four synthetic steps in overall yields ranging from 17 to 80%.