methyl 6-((2R,5S,6S)-5,6-dihydroxy-1-tosylpiperidin-2-yl)-hexanoate | 1427307-10-5

• 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: methyl 6-((2R,5S,6S)-5,6-dihydroxy-1-tosylpiperidin-2-yl)-hexanoate
• 英文别名: methyl 6-[(2R,5S,6S)-5,6-dihydroxy-1-(4-methylphenyl)sulfonylpiperidin-2-yl]hexanoate
• CAS: 1427307-10-5
• 化学式: C₁₉H₂₉NO₆S
• 分子量: 399.508
• InChiKey: QMHCMHRSUJXZEA-AYBZRNKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-((R)-1,2,3,4-tetrahydro-1-tosylpyridin-2-yl)hexanal 在 potassium osmate(VI) 、 甲基磺酰胺 、 水 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 甲苯 为溶剂， 反应 3.0h， 生成 methyl 6-((2R,5S,6S)-5,6-dihydroxy-1-tosylpiperidin-2-yl)-hexanoate 、 methyl 6-((2R,5R,6S)-5,6-dihydroxy-1-tosylpiperidin-2-yl)-hexanoate
  参考文献：
  名称：

  Synthesis of azimic acid using hydroformylation

  摘要：

  A synthesis of the alkaloid azimic acid has been achieved using double hydroformylation with a single tandem condensation to form the six membered ring. The oxygen substituent was introduced by diastereoselective dihydroxylation, cis to the existing alkyl substituent The methyl substituent was introduced via an iminium ion intermediate under stereoelectronic control. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.060

文献信息

• Synthesis of azimic acid using hydroformylation
  作者：Roderick W. Bates、Sivarajan Kasinathan

  DOI：10.1016/j.tet.2013.01.060

  日期：2013.4

  A synthesis of the alkaloid azimic acid has been achieved using double hydroformylation with a single tandem condensation to form the six membered ring. The oxygen substituent was introduced by diastereoselective dihydroxylation, cis to the existing alkyl substituent The methyl substituent was introduced via an iminium ion intermediate under stereoelectronic control. (C) 2013 Elsevier Ltd. All rights reserved.