methyl 5-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside | 484678-85-5

• 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: methyl 5-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside
• 英文别名: methyl (2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-2-(phenylmethoxymethyl)oxolane-2-carboxylate
• CAS: 484678-85-5
• 化学式: C₂₁H₃₄O₆Si
• 分子量: 410.583
• InChiKey: GZDSIHDQTSUSCC-KXXXGBTESA-N

物化性质

• 沸点：
  439.0±45.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside 在 四丁基氟化铵 、 四氯化锡 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 72.83h， 生成 1-[(2R,3S,5R)-5-(6-Amino-purin-9-yl)-2-benzyloxymethyl-3-hydroxy-tetrahydro-furan-2-yl]-2,2-dimethyl-propan-1-one
  参考文献：
  名称：

  通过将位点选择性注入腺嘌呤而触发DNA的电荷转移。

  摘要：

  正电荷被选择性地注入DNA双链的腺嘌呤（A）中，并以与距离无关的方式沿着（A：T）n序列迁移。

  DOI：

  10.1039/b205928b
• 作为产物：
  描述：

  methyl (2R,3S)-3,5-dihydroxy-2-(phenylmethoxymethyl)oxolane-2-carboxylate 在 盐酸 作用下， 生成 methyl 5-O-benzyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside
  参考文献：
  名称：

  A Convenient Asymmetric Synthesis of 4‘-α-Carboxylated Nucleosides

  摘要：

  DOI：

  10.1021/jo980301f

文献信息

• Asymmetric Synthesis of C4‘α-Carboxylated 2‘-Deoxynucleosides. Preparation of Oxetanone Derivatives and Influence of Solvent on the Stereochemistry of Base Introduction
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo990046e

  日期：1999.5.1

  A synthesis of methyl 5-O-benzyl-3-O-tert-butyldimethylsilyl-4 alpha-methoxycarbonyl-2-deoxyribofuranoside from dimethyl L-tartrate is presented. Coupling of this substance with standard purine and pyrimidine bases, promoted by tin tetrachloride, provides the corresponding 4'alpha-methoxycarbonylnucleosides with moderate yield and selectivity. A series of related bicyclic donors, derived by forming a beta-lactone between the 3-OH and the 4 alpha-carboxy group, were prepared and assayed in coupling reactions. In nonpolar solvents good endo-selectivity is observed whereas in acetonitrile the exoanomers are preferentially obtained. Methods for the removal of the 5'-O-benzyl ethers of the nucleosides are presented.
• Charge transfer through DNA triggered by site selective charge injection into adenine
  作者：Thomas Kendrick、Bernd Giese

  DOI：10.1039/b205928b

  日期：2002.9.11

  A positive charge, which was injected site selectively into adenine (A) of a DNA double strand, migrates along (A:T)n sequences in a distance independent way.

  正电荷被选择性地注入DNA双链的腺嘌呤（A）中，并以与距离无关的方式沿着（A：T）n序列迁移。
• A Convenient Asymmetric Synthesis of 4‘-α-Carboxylated Nucleosides
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo980301f

  日期：1998.6.1