Bn(-3)[TBDMS(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl | 1042907-58-3

• 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: Bn(-3)[TBDMS(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl
• 英文别名: 1-[(2R,4S,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylmethoxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1042907-58-3
• 化学式: C₂₃H₃₄N₂O₅Si
• 分子量: 446.619
• InChiKey: NBBDTDLIFYQGLM-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  31
• 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：
  77.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  溴甲苯 、 5’-O-(叔丁基二甲基甲硅烷基)胸苷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.28h， 以82%的产率得到Bn(-3)[TBDMS(-5)]2-deoxy-D-eryPenf(b)-thymin-1-yl
  参考文献：
  名称：

  Solvent-controlled regioselective protection of 5′-O-protected thymidine

  摘要：

  This paper describes an efficient procedure for selective 3'-O- or 3-N-protection of 5'-O-tert-butyldimethylsilylthymidine, depending on the use of aprotic polar solvents with low or high dielectric constant, respectively. These syntheses were activated by either ultrasound or microwaves. Several alkyl bromides offer a convenient route to prepare 3'-O- or 3-N-protected and functionalized thymidine derivatives. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.026

文献信息

• Solvent-controlled regioselective protection of 5′-O-protected thymidine
  作者：K. Teste、L. Colombeau、A. Hadj-Bouazza、R. Lucas、R. Zerrouki、P. Krausz、Y. Champavier

  DOI：10.1016/j.carres.2008.04.026

  日期：2008.7

  This paper describes an efficient procedure for selective 3'-O- or 3-N-protection of 5'-O-tert-butyldimethylsilylthymidine, depending on the use of aprotic polar solvents with low or high dielectric constant, respectively. These syntheses were activated by either ultrasound or microwaves. Several alkyl bromides offer a convenient route to prepare 3'-O- or 3-N-protected and functionalized thymidine derivatives. (C) 2008 Elsevier Ltd. All rights reserved.