(2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde | 1393478-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde
• CAS: 1393478-30-2
• 化学式: C₂₅H₃₂O₄Si
• 分子量: 424.612
• InChiKey: NLGQJZRGRVJTPM-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 60.5h， 生成 (3aS,5aS,8aS,8bS)-6-tert-butyl-2,2-dimethyl-3a,5a,8a,8b-tetrahydro-[1,3]dioxolo[4,5-g][1,3]benzoxazol-7-one
  参考文献：
  名称：

  A Chiron Approach to Aminocytitols by Petasis-Borono-Mannich Reaction: Formal Synthesis of (+)-Conduramine E and (−)-Conduramine E

  摘要：

  A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-beta-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.

  DOI：

  10.1021/jo300804d
• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-α-D-galactopyranoside 在 咪唑 、 vitamin B12 、 碘 、 氯化铵 、 三苯基膦 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.08h， 生成 (2R)-2-[tert-butyl(diphenyl)silyl]oxy-2-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde
  参考文献：
  名称：

  A Chiron Approach to Aminocytitols by Petasis-Borono-Mannich Reaction: Formal Synthesis of (+)-Conduramine E and (−)-Conduramine E

  摘要：

  A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-beta-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.

  DOI：

  10.1021/jo300804d

文献信息

• A Chiron Approach to Aminocytitols by Petasis-Borono-Mannich Reaction: Formal Synthesis of (+)-Conduramine E and (−)-Conduramine E
  作者：Partha Ghosal、Arun K. Shaw

  DOI：10.1021/jo300804d

  日期：2012.9.7

  A chiron approach to a stereoselective route for the synthesis of aminocytitols from carbohydrates is described. The formal synthesis of (+)-conduramine E and (-)-conduramine E was achieved by utilizing this strategy. The key features of the synthetic strategy include one-pot three-component Petasis-Borono-Mannich reaction to introduce the syn-beta-amino alcohol functionality of conduramine E and ring-closing metathesis to construct its carbocyclic core. The present synthetic approach paves the way for stereoselective synthesis of several conduramines starting from carbohydrates.