[(3aR,4R,5S,6aR)-5-hydroxy-2,2,5-trimethyl-3a-[(4-methylphenyl)sulfonyloxymethyl]-6,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-yl]methyl 4-methylbenzenesulfonate | 276246-09-4

• 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: [(3aR,4R,5S,6aR)-5-hydroxy-2,2,5-trimethyl-3a-[(4-methylphenyl)sulfonyloxymethyl]-6,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 276246-09-4
• 化学式: C₂₅H₃₂O₉S₂
• 分子量: 540.656
• InChiKey: DDPARZLEONMHHY-SDZTWWDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  [(3aR,4R,5S,6aR)-5-hydroxy-2,2,5-trimethyl-3a-[(4-methylphenyl)sulfonyloxymethyl]-6,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-yl]methyl 4-methylbenzenesulfonate 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 96.0h， 生成 (3aR,5S,5aR,8aR)-2,2,5-Trimethyl-hexahydro-1,3-dioxa-7-aza-cyclopenta[c]pentalen-5-ol
  参考文献：
  名称：

  Conversion of the Iridoid Glucoside Antirrhinoside into 3-Azabicyclo[3.3.0]octane Building Blocks

  摘要：

  The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.

  DOI：

  10.1021/np9905517
• 作为产物：
  描述：

  5,6:4',6'-di-O-isopropylidene-antirrhinoside 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 [(3aR,4R,5S,6aR)-5-hydroxy-2,2,5-trimethyl-3a-[(4-methylphenyl)sulfonyloxymethyl]-6,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Conversion of the Iridoid Glucoside Antirrhinoside into 3-Azabicyclo[3.3.0]octane Building Blocks

  摘要：

  The iridoid glucoside antirrhinoside (1) was transformed into polysubstituted 3-azabicyclo[3.3.0]octanes 3, 12, and 13 in 4 to 5 steps. Ozonolysis of the diacetonide of 1 and of its 7-deoxy-derivative 8 afforded cyclopentanoids 2 and 10, respectively. Conditions for the selective conversion of 2 and 10 into the corresponding ditosylates 4 and 11 were investigated. Cyclization of 4 and 11 was achieved with benzylamine and 2-methoxybenzylamine to yield bicyclic pyrrolidines 3, 12, and 13. Additional building blocks 14 and 15 were obtained by selective deprotection of the N-benzyl and isopropylidene moieties in 12 and 13, respectively.

  DOI：

  10.1021/np9905517