2R,3S-2-benzyloxymethyl-3-hydroxymethyl-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane | 208175-28-4

• 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: 2R,3S-2-benzyloxymethyl-3-hydroxymethyl-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane
• 英文别名: methyl (2S,3R)-2-(hydroxymethyl)-3-(phenylmethoxymethyl)-1,4-dioxaspiro[4.4]nonane-3-carboxylate
• CAS: 208175-28-4
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: UAHJTQNRFVSHLT-MAUKXSAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2R,3S-2-benzyloxymethyl-3-hydroxymethyl-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 lithium diisopropyl amide 作用下， 生成 2R,3S-2-benzyloxymethyl-3-<2,2-di(methoxy)ethyl>-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane
  参考文献：
  名称：

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

  摘要：

  DOI：

  10.1021/jo980301f
• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 在 二异丁基氢化铝 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 甲苯 、 苯 为溶剂， 反应 12.0h， 生成 2R,3S-2-benzyloxymethyl-3-hydroxymethyl-2-methoxycarbonyl-1,4-dioxaspiro<4.4>nonane
  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

• 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