{(4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolan-4-yl}methanol | 1014651-13-8

• 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: {(4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolan-4-yl}methanol
• 英文别名: [(4R,5S)-2,2-dimethyl-5-[(E)-3-phenylprop-2-enyl]-1,3-dioxolan-4-yl]methanol
• CAS: 1014651-13-8
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: XVWBQTPKZPIXBH-YESVKVCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {(4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolan-4-yl}methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 反应 4.0h， 以85%的产率得到(4S,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Rapid Assembly of the Polyhydroxylated β-Amino Acid Constituents of Microsclerodermins C, D, and E

  摘要：

  A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.

  DOI：

  10.1021/ol702962z
• 作为产物：
  描述：

  苯基膦酸二乙酯 、 3,4-O-isopropylidene-2-deoxy-D-ribose 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.0h， 以52%的产率得到{(4R,5S)-2,2-dimethyl-5-[(E)-3-phenylallyl]-1,3-dioxolan-4-yl}methanol
  参考文献：
  名称：

  Rapid Assembly of the Polyhydroxylated β-Amino Acid Constituents of Microsclerodermins C, D, and E

  摘要：

  A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.

  DOI：

  10.1021/ol702962z

文献信息

• Rapid Assembly of the Polyhydroxylated β-Amino Acid Constituents of Microsclerodermins C, D, and E
  作者：Thomas Hjelmgaard、Sophie Faure、Pascale Lemoine、Bernard Viossat、David J. Aitken

  DOI：10.1021/ol702962z

  日期：2008.3.1

  A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated beta-amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines.