4-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-cytidine | 208175-44-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-cytidine
• 英文别名: methyl (2R,3S,5R)-5-(4-acetamido-2-oxopyrimidin-1-yl)-3-[tert-butyl(dimethyl)silyl]oxy-2-(phenylmethoxymethyl)oxolane-2-carboxylate
• CAS: 208175-44-4
• 化学式: C₂₆H₃₇N₃O₇Si
• 分子量: 531.681
• InChiKey: IWANCQXKURIMIA-UNIVCBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-cytidine 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到(2R,3S,5R)-5-(4-Amino-2-oxo-2H-pyrimidin-1-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
• 作为产物：
  描述：

  methyl 5-O-benzyl-2-deoxy-4α-methoxycarbonyl-α,β-D-ribo-pentofuranoside 在 四氯化锡 作用下， 以 乙腈 为溶剂， 生成 4-N-acetyl-5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-4'α-methoxycarbonyl-D-cytidine
  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

• 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.