(-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine | 177341-40-1

• 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: (-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine
• 英文别名: benzyl (2R,4S,6S)-2-(acetyloxymethyl)-4-(methoxymethoxy)-6-(methoxymethoxymethyl)piperidine-1-carboxylate
• CAS: 177341-40-1
• 化学式: C₂₁H₃₁NO₈
• 分子量: 425.479
• InChiKey: STYDJLADQBJBHR-ZCNNSNEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到(5S,7S,8aR)-7-(methoxymethoxy)-5-(methoxymethoxymethyl)-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：

  (2S,4S,6R)-4-Hydroxy-piperidine-1,2,6-tricarboxylic acid benzyl ester dimethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 、 potassium dihydrogenphosphate 、 锂硼氢 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 137.5h， 生成 (-)-N-(benzyloxycarnonyl)-cis,cis-2(R)-(acetoxymethyl)-4(S)-(methoxymethoxy)-6(S)-<(methoxymethoxy)methyl>piperidine
  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

• Chemoenzymatic Synthesis of Both Enantiomers of <i>cis</i>-6-(Hydroxymethyl)- and <i>cis,cis</i>-4-Hydroxy-6-(hydroxymethyl)pipecolic Acids
  作者：Robert Chênevert、Marie-Pascale Morin

  DOI：10.1021/jo9823036

  日期：1999.4.1

  Both enantiomers of cis-6-(hydroxymethyl)- and cis,cis-4-hydroxy-6-(hydroxymethyl)pipecolic acids, piperidine-based nonproteinogenic amino acids, have been synthesized from starting materials obtained from enzymatic desymmetrizations.

  顺式6-（羟甲基）-和顺式-顺式-4-羟基-6-（羟甲基）哌酸的对映异构体都是基于哌啶的非蛋白原性氨基酸，是从酶解对称法获得的起始原料合成的。