3',5'-O-(tetraisopropyl-disiloxane-1,3-diyl)-2'-O-phenoxythiocarbonyl-uridine | 76700-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',5'-O-(tetraisopropyl-disiloxane-1,3-diyl)-2'-O-phenoxythiocarbonyl-uridine
• 英文别名: 1-[(6aR,8R,9R,9aR)-9-phenoxycarbothioyloxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]pyrimidine-2,4-dione
• CAS: 76700-78-2
• 化学式: C₂₈H₄₂N₂O₈SSi₂
• 分子量: 622.887
• InChiKey: OBIONWAMJSNGCL-VNSJUHMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.14
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3',5'-O-(tetraisopropyl-disiloxane-1,3-diyl)-2'-O-phenoxythiocarbonyl-uridine 在 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 2-脱氧尿苷
  参考文献：
  名称：

  Smooth and efficient deoxygenation of secondary alcohols. A general procedure for the conversion of ribonucleosides to 2'-deoxynucleosides

  摘要：

  DOI：

  10.1021/ja00394a033
• 作为产物：
  描述：

  尿嘧啶核苷 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 3',5'-O-(tetraisopropyl-disiloxane-1,3-diyl)-2'-O-phenoxythiocarbonyl-uridine
  参考文献：
  名称：

  使用闭环烯烃和烯炔复分解反应合成构象受限的核酸片段

  摘要：

  为了构建用于识别二级 RNA 结构的构象限制性核酸片段，我们合成了不同的含有额外环的单核苷酸和二核苷酸。这些环是通过从已引入双键或三键的核苷酸底物通过闭环烯烃或烯炔复分解反应制备的。

  DOI：

  10.1081/ncn-200060347

文献信息

• Nucleic acid related compounds. 42. A general procedure for the efficient deoxygenation of secondary alcohols. Regiospecific and stereoselective conversion of ribonucleosides to 2'-deoxynucleosides
  作者：Morris J. Robins、John S. Wilson、Fritz Hansske

  DOI：10.1021/ja00350a052

  日期：1983.6
• Groetli, Morten; Undheim, Kjell, Acta Chemica Scandinavica, 1995, vol. 49, # 3, p. 217 - 224
  作者：Groetli, Morten、Undheim, Kjell

  DOI：——

  日期：——
• Selective site deuteration on the sugar ring as an efficient marker of conformation in nucleosides: The CD stretching mode of the (2′-R)-[2′-2H]-2′-deoxyuridine and its 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-derivative
  作者：L. Grajcar、M.H. Baron、S. Becouarn、S. Czernecki、J.M. Valery、C. Reiss

  DOI：10.1016/0584-8539(94)80022-7

  日期：1994.6

  A uridine specifically deuterated on the deoxyribose ring at the C2', and the same compound in a more rigid form, due to a chemically fused ring (between C3' and C5'), have been synthesized. By NMR, the coupling constants J1'-2' and J3'-4' have been determined and the populations of the C2'-endo and C3'-endo conformers have been deduced for the two compounds. Comparison of these results with an FTIR and Raman study of the stretching mode nuC-D on the C2' site allows a specific assignment of each observed band to one of the two classes of conformers. This enables us to consider the further step: the direct recognition, by IR and Raman spectroscopies, of the local conformation at a specific site of a synthetic oligonucleotide, using the nuCD signals as marker bands.
• Tris(trimethylsilyl)[2H]silane-triethylborane system producing the highly diastereoselective deuteration (> 99:1) of 2′-bromo-2′-deoxy- and 2′-O-phenoxythiocarbonylribonucleosides at 0°C
  作者：Etsuko Kawashima、Seishiro Uchida、Masayoshi Miyahara、Yoshiharu Ishido

  DOI：10.1016/s0040-4039(97)01722-x

  日期：1997.10

  Reductive protylation and deuteration reactions using (Me3Si)(3)SiH- and (Me3Si)(3)(SiH)-H-2-Et3B systems were investigated in view of the differences in bond energy and bond length between the Si-H of (Me3Si)(3)SiH and the Sn-H of Bu3SnH. Higher diastereoselectivity was obtained in comparison with the reactions using the Bu3SnH - and (Bu3SnH)-H-2-Et3B systems; the (Me3Si)(3)SiH system gave remarkable diastereoselectivity of 98.7% at 0 degrees C, whereas the other system required temperatures below -70 degrees C. (C) 1997 Elsevier Science Ltd.