benzyl N-[(3S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl]carbamate | 159267-73-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl N-[(3S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl]carbamate
• CAS: 159267-73-9
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: IFVAREYHRQIELQ-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(3S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl]carbamate 在 双(乙腈)氯化钯(II) 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 [(3S,5S)-5-((R)-1,2-Dihydroxy-ethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Optically Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes

  摘要：

  Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.

  DOI：

  10.1021/ja00101a014
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 palladium dihydroxide 盐酸 、 正丁基锂 、 air 、 一氧化碳 、 氢气 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 25.5h， 生成 benzyl N-[(3S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-oxooxolan-3-yl]carbamate
  参考文献：
  名称：

  Synthesis of Optically Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes

  摘要：

  Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.

  DOI：

  10.1021/ja00101a014

文献信息

• Synthesis of Optically Active 4-Substituted 2-Aminobutyrolactones and Homoserines by Combined Aldol/Photocyclization Reactions of Chromium Aminocarbene Complexes
  作者：Carsten Schmeck、Louis S. Hegedus

  DOI：10.1021/ja00101a014

  日期：1994.11

  Aldol reactions of optically active chromium aminocarbene complexes proceeded with moderate to high diastereoselectivity. Photolysis of the aldol product gave optically active 4-substituted 2-aminobutyrolactones which could be hydrolyzed to gamma-hydroxy-alpha-amino acids. Using this procedure, (+)-bulgecenine was synthesized.