((3aR,4R,7S,7aR)-4-Methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetic acid ethyl ester | 182687-84-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((3aR,4R,7S,7aR)-4-Methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetic acid ethyl ester
• CAS: 182687-84-9
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: CVAYEYPVUPFNAP-JTLRNRKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((3aR,4R,7S,7aR)-4-Methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetic acid ethyl ester 在 sodium tetrahydroborate 、 氧气 、 二异丁基氢化铝 、 臭氧 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 4-deoxy-4-C-hydroxymethyl-2,3-O-isopropylidene-1-O-methyl-α-L-lyxopyranose
  参考文献：
  名称：

  Synthesis of 4-Deoxy-4-C-hydroxymethyl-α-L-Lyxo-Pyranosyl Thymine

  摘要：

  The synthesis of 1-[4-deoxy-4-C-hydroxymethyl-alpha-L-lyxopyranosy]thymine has been accomplished by two synthetic routes both starting from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside. The first route makes use of a ring opening, ring closure reaction sequence to increase the proportion of the desired L-isomers. The second route utilizes the soft nucleophilic character of malonyl anions and ozonolytic cleavage of enol ether to introduce the branched chain. The newly obtained pyranosyl nucleoside obtains a C-4(1) conformation with an equatorially oriented thymine moiety.

  DOI：

  10.1080/07328319608002450
• 作为产物：
  描述：

  diethyl 2-[(3aR,4R,7S,7aR)-4-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-yl]propanedioate 在 lithium chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 以7.74 g的产率得到((3aR,4R,7S,7aR)-4-Methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 4-Deoxy-4-C-hydroxymethyl-α-L-Lyxo-Pyranosyl Thymine

  摘要：

  The synthesis of 1-[4-deoxy-4-C-hydroxymethyl-alpha-L-lyxopyranosy]thymine has been accomplished by two synthetic routes both starting from methyl 2,3-O-isopropylidene-beta-D-ribopyranoside. The first route makes use of a ring opening, ring closure reaction sequence to increase the proportion of the desired L-isomers. The second route utilizes the soft nucleophilic character of malonyl anions and ozonolytic cleavage of enol ether to introduce the branched chain. The newly obtained pyranosyl nucleoside obtains a C-4(1) conformation with an equatorially oriented thymine moiety.

  DOI：

  10.1080/07328319608002450