(+)-epiallo muscarine iodide | 5487-32-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-epiallo muscarine iodide
• 英文别名: [(2R,4S,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl-trimethylazanium;iodide
• CAS: 5487-32-1
• 化学式: C₉H₂₀NO₂*I
• 分子量: 301.168
• InChiKey: PMFYONXEPDMBPE-HBJOHWKNSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -2.77
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,6-di-O-p-tolylsulfonyl-2,5-anhydro-L-idofuranose dimethylacetal 在 4-二甲氨基吡啶 盐酸 、 lithium aluminium tetrahydride 、 jones reagent 、 草酰氯 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 丙酮 、 甲苯 为溶剂， 反应 29.0h， 生成 (+)-epiallo muscarine iodide
  参考文献：
  名称：

  Synthesis of (2R,4S,5S)-epiallomuscarine, (2S,3R,5S)-isoepiallomuscarine, and (2S,3S,4S,5S)-3-hydroxyepiallomuscarine from .alpha.-D-glucose

  摘要：

  DOI：

  10.1021/jo01314a031

文献信息

• Chemoenzymic synthesis of the eight stereoisomeric muscarines
  作者：Marco De Amici、Carlo De Micheli、Giorgio Molteni、Davide Pitre、Giacomo Carrea、Sergio Riva、Sandro Spezia、Lucia Zetta

  DOI：10.1021/jo00001a015

  日期：1991.1

  Efficient syntheses of the eight stereoisomers of muscarine have been accomplished by dehydrogenase-catalyzed reduction of iodo ketones (+/-)-3a and (+/-)-3b. 3-alpha,20-beta-Hydroxysteroid dehydrogenase from Streptomyces hydrogenans exhibited high enantiomeric and diastereotopic selectivity for (+/-)-3a, yielding an equimolar mixture of iodo alcohol (-)-4 (2S,4S,5S) (96% ee) and iodo ketone (+)-3a (2R,5R) (96% ee) which was reduced by sodium borohydride to a mixture of (+)-4 and (+)-5. 3-beta,17-beta-Hydroxysteroid dehydrogenase from Pseudomonas testosteroni reduced (+/-)-3b with high diastereotopic selectivity to give an equimolar mixture of iodo alcohols (+)-6 (2R,4S,5S) (> 99% ee) and (-)-7 (2S,4S,5R) (81% ee). Synthesis of the remaining iodo alcohols [(-)-5, (-)-6, and (+)-7] was achieved by applying the Mitsunobu procedure to (-)-4, (-)-7, and (+)-6. The enantiomeric excess of intermediates 4-7 was determined by HPLC analysis of the (R)-(+)-MTPA esters. The chiral iodo alcohols 4-7 were then transformed into the final derivatives by conventional chemical manipulations.
• DE, AMICI MARCO;DE, MICHELI CARLO;MOLTENI, GIORGIO;PITRE, DAVIDE;CARREA, +, J. ORG. CHEM., 56,(1991) N, C. 67-72
  作者：DE, AMICI MARCO、DE, MICHELI CARLO、MOLTENI, GIORGIO、PITRE, DAVIDE、CARREA, +

  DOI：——

  日期：——
• Synthesis of (2R,4S,5S)-epiallomuscarine, (2S,3R,5S)-isoepiallomuscarine, and (2S,3S,4S,5S)-3-hydroxyepiallomuscarine from .alpha.-D-glucose
  作者：Pen-Chung Wang、Madeleine M. Joullie

  DOI：10.1021/jo01314a031

  日期：1980.12