5'-O-benzyl-6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-adenosine | 208175-48-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 5'-O-benzyl-6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-adenosine
• 英文别名: methyl (2R,3S,5R)-5-(6-benzamidopurin-9-yl)-3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxymethyl)oxolane-2-carboxylate
• CAS: 208175-48-8
• 化学式: C₃₂H₃₉N₅O₆Si
• 分子量: 617.777
• InChiKey: HWBBODOLSBCCAV-BRUQSJHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5'-O-benzyl-6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-adenosine 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 potassium tert-butylate 、 碘 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 3.83h， 生成 5'-O-benzyl-4'α-[(2-(2-bromophenyl)-2-methylpropylthio)carbonyl]-2'-deoxy-3'-O-diethylphosphoryladenosine
  参考文献：
  名称：

  The effect of the base in the fragmentation of nucleotide C4′ radicals

  摘要：

  A series of 3'-O-diethylphosphoryl-4'-alpha-[(2-halophenylethylthio)carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4'-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4'-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A (119)Sn NMR method is presented for estimation of the purity of tin hydride solutions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00557-4
• 作为产物：
  描述：

  methyl (2R,3S)-3,5-dihydroxy-2-(phenylmethoxymethyl)oxolane-2-carboxylate 在 盐酸 、 四氯化锡 作用下， 以 乙腈 为溶剂， 生成 5'-O-benzyl-6-N-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-adenosine
  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.
• A Convenient Asymmetric Synthesis of 4‘-α-Carboxylated Nucleosides
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo980301f

  日期：1998.6.1
• The effect of the base in the fragmentation of nucleotide C4′ radicals
  作者：David Crich、Dae-Hwan Suk、Xiaolin Hao

  DOI：10.1016/s0040-4020(02)00557-4

  日期：2002.7

  A series of 3'-O-diethylphosphoryl-4'-alpha-[(2-halophenylethylthio)carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4'-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4'-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A (119)Sn NMR method is presented for estimation of the purity of tin hydride solutions. (C) 2002 Elsevier Science Ltd. All rights reserved.