(2R,3S,5S)-5-(6-Benzoylamino-purin-9-yl)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester | 208175-23-9

• 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: (2R,3S,5S)-5-(6-Benzoylamino-purin-9-yl)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester
• 英文别名: methyl (2R,3S,5S)-5-(6-benzamidopurin-9-yl)-3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxymethyl)oxolane-2-carboxylate
• CAS: 208175-23-9
• 化学式: C₃₂H₃₉N₅O₆Si
• 分子量: 617.777
• InChiKey: HWBBODOLSBCCAV-PNRGXICFSA-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：

  (2R,3S,5S)-5-(6-Benzoylamino-purin-9-yl)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以50%的产率得到6-N-benzyl-1-<2S,3S,5S-2-benzyloxymethyl-3-(tert-butyldimethylsiloxy)-2-methoxycarbobyl-5-tetrahydrofuranyl>adenine
  参考文献：
  名称：

  Asymmetric Synthesis of C4‘α-Carboxylated 2‘-Deoxynucleosides. Preparation of Oxetanone Derivatives and Influence of Solvent on the Stereochemistry of Base Introduction

  摘要：

  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.

  DOI：

  10.1021/jo990046e
• 作为产物：
  描述：

  methyl 5-O-benzyl-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside 在 2,6-二甲基吡啶 、 N,O-双三甲硅基乙酰胺 、 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3S,5S)-5-(6-Benzoylamino-purin-9-yl)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of C4‘α-Carboxylated 2‘-Deoxynucleosides. Preparation of Oxetanone Derivatives and Influence of Solvent on the Stereochemistry of Base Introduction

  摘要：

  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.

  DOI：

  10.1021/jo990046e

文献信息

• A Convenient Asymmetric Synthesis of 4‘-α-Carboxylated Nucleosides
  作者：David Crich、Xiaolin Hao

  DOI：10.1021/jo980301f

  日期：1998.6.1
• 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.