(2R,4S,6S)-2,6-Bis-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester | 177341-36-5

• 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,4S,6S)-2,6-Bis-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester
• CAS: 177341-36-5
• 化学式: C₁₇H₂₅NO₆
• 分子量: 339.389
• InChiKey: DYCTWZAJYUVULY-MUJYYYPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  88.46
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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 、 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 122.5h， 生成 (5S,7S,8aR)-7-hydroxy-5-(hydroxymethyl)-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
  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)-4-Methoxymethoxy-piperidine-1,2,6-tricarboxylic acid benzyl ester dimethyl ester 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以93%的产率得到(2R,4S,6S)-2,6-Bis-hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid benzyl ester
  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

文献信息

• Enzymatic desymmetrization of meso cis-2,6- and cis,cis-2,4,6-substituted piperidines. Chemoenzymatic synthesis of (5S,9S)-(+)-indolizidine 209D
  作者：Robert Chênevert、Ghodsi Mohammadi Ziarani、Marie Pascale Morin、Mohammed Dasser

  DOI：10.1016/s0957-4166(99)00315-8

  日期：1999.8

  The stereoselective acylation of meso piperidines 3a,b by vinyl acetate (solvent and acyl donor) in the presence of Candida antarctica lipase gave the corresponding (2S,6R) and (2S,4R,6R) monoesters 2a,b in high enantiomeric purity. (5S,9S)-(+)-Indolizidine 209D was prepared in eight steps from (2S,6R)-2a. (C) 1999 Elsevier Science Ltd. All rights reserved.