[(5S,7R,8aR)-7-methylsulfonyloxy-3-oxo-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-5-yl]methyl methanesulfonate | 177341-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: [(5S,7R,8aR)-7-methylsulfonyloxy-3-oxo-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-5-yl]methyl methanesulfonate
• CAS: 177341-43-4
• 化学式: C₁₀H₁₇NO₈S₂
• 分子量: 343.379
• InChiKey: SJSGTRSFQUWIIW-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(5S,7R,8aR)-7-methylsulfonyloxy-3-oxo-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-5-yl]methyl methanesulfonate 在 氢氧化钾 、 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 51.0h， 生成 [(2R,6R)-1-benzyl-6-methylpiperidin-2-yl]methanol
  参考文献：
  名称：

  Enzymatic Route to Chiral, Nonracemic cis-2,6- and cis,cis-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D

  摘要：

  Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase(ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee greater than or equal to 98%). The general method is used to effect the synthesis of (+)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.

  DOI：

  10.1021/jo9519569
• 作为产物：
  描述：

  (2R,4S,6S)-2,6-Bis-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 potassium dihydrogenphosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 126.5h， 生成 [(5S,7R,8aR)-7-methylsulfonyloxy-3-oxo-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-5-yl]methyl methanesulfonate
  参考文献：
  名称：

  Enzymatic Route to Chiral, Nonracemic cis-2,6- and cis,cis-2,4,6-Substituted Piperidines. Synthesis of (+)-Dihydropinidine and Dendrobate Alkaloid (+)-241D

  摘要：

  Piperidine-based compounds are an important class of natural alkaloids found in plants, insects, and amphibians. A general asymmetric synthesis of 2-alkyl-6-methylpiperidines is presented via the enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines with Aspergillus niger lipase(ANL). The enzymatic reaction proceeds in excellent chemical yield and high enantiotopic selectivity (ee greater than or equal to 98%). The general method is used to effect the synthesis of (+)-dihydropinidine-HCl as well as the first asymmetric synthesis of dendrobate alkaloid (+)-241D.

  DOI：

  10.1021/jo9519569