dimethyl 2,3-O-cyclopentylidene-L-tartrate | 198691-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl 2,3-O-cyclopentylidene-L-tartrate
• 英文别名: dimethyl (2R,3R)-1,4-dioxaspiro[4.4]nonane-2,3-dicarboxylate
• CAS: 198691-38-2
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: XSBLKWNNBFDUMD-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,3-O-cyclopentylidene-L-tartrate 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 二异丁基氢化铝 、 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 、 1,1-二甲氧基环戊烷 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 12.0h， 以90%的产率得到dimethyl 2,3-O-cyclopentylidene-L-tartrate
  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

• Highly isotactic optically active methacrylate polymers by free radical cyclopolymerization
  作者：Shiying Zheng、Dotsevi Y. Sogah

  DOI：10.1016/s0040-4020(97)00974-5

  日期：1997.11

  Isospecific free radical cyclopolymerization of tartrate-based monomers gives polymers with very high optical rotations. Circular dichroism and polarimetric measurements suggest the polymers are rigid and ordered. Their high resistance to solvolysis suggests potential applications in chiral chromatography.

  基于酒石酸酯的单体的异种自由基环聚合反应使聚合物具有非常高的旋光度。圆二色性和极化测量表明聚合物是刚性的和有序的。它们对溶剂分解的高抵抗力表明其在手性色谱法中的潜在应用。
• 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