1R,3R,5S-1-(benzyloxymethyl)-2,6-dioxa-7-oxo-3-(4-pentenyloxy)bicyclo<3.2.0>heptane | 223923-76-0

• 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: 1R,3R,5S-1-(benzyloxymethyl)-2,6-dioxa-7-oxo-3-(4-pentenyloxy)bicyclo<3.2.0>heptane
• 英文别名: (1R,3S,5S)-3-pent-4-enoxy-1-(phenylmethoxymethyl)-2,6-dioxabicyclo[3.2.0]heptan-7-one
• CAS: 223923-76-0
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: ZCBPUBJXFQZJGK-XYJFISCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1R,3R,5S-1-(benzyloxymethyl)-2,6-dioxa-7-oxo-3-(4-pentenyloxy)bicyclo<3.2.0>heptane 在 溴 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,5S)-1-Benzyloxymethyl-3-bromo-2,6-dioxa-bicyclo[3.2.0]heptan-7-one
  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 (2R,3S)-3,5-dihydroxy-2-(phenylmethoxymethyl)oxolane-2-carboxylate 在 lithium hydroxide 、 camphor-10-sulfonic acid 、 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 为溶剂， 反应 13.0h， 生成 1R,3R,5S-1-(benzyloxymethyl)-2,6-dioxa-7-oxo-3-(4-pentenyloxy)bicyclo<3.2.0>heptane
  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