(3S,4R,2'S,5'S,6'R)-1-(4-methoxyphenyl)-4-phenyl-3-[(2',4',5'-trimethyl-3'-oxo-6'-phenylmorpholin-2'-yl)oxy]azetidin-2-one | 523987-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3S,4R,2'S,5'S,6'R)-1-(4-methoxyphenyl)-4-phenyl-3-[(2',4',5'-trimethyl-3'-oxo-6'-phenylmorpholin-2'-yl)oxy]azetidin-2-one
• 英文别名: (2R,5S,6R)-2-[(3S,4R)-1-(4-methoxyphenyl)-2-oxo-4-phenylazetidin-3-yl]oxy-2,4,5-trimethyl-6-phenylmorpholin-3-one
• CAS: 523987-56-6
• 化学式: C₂₉H₃₀N₂O₅
• 分子量: 486.568
• InChiKey: BYLSZMGEMCMBNB-UUMGPOKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  68.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,2'S,5'S,6'R)-1-(4-methoxyphenyl)-4-phenyl-3-[(2',4',5'-trimethyl-3'-oxo-6'-phenylmorpholin-2'-yl)oxy]azetidin-2-one 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.0h， 以90%的产率得到(+/-)-cis-3-hydroxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone
  参考文献：
  名称：

  Ephedrine derived reusable chiral auxiliary for the synthesis of optically pure 3-hydroxy-4-aryl-β-lactams

  摘要：

  The diastereoselective synthesis of carious beta-lactams has been achieved using a chit-at acid auxiliary derived from (-)-ephedrine. An efficient acid-catalyzed cleavage of the chiral auxiliary from these beta-lactams to afford 3-hydroxy-4-aryl-cis-beta-lactams. which are precursors for analogues Of the taxol side chain, is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00039-9
• 作为产物：
  描述：

  ethyl (2S,5S,6R)-[(2,4,6-trimethyl-3-oxo-6-phenylmorpholin-2-yl)oxy]acetate 在 sodium hydroxide 、 三光气 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (3S,4R,2'S,5'S,6'R)-1-(4-methoxyphenyl)-4-phenyl-3-[(2',4',5'-trimethyl-3'-oxo-6'-phenylmorpholin-2'-yl)oxy]azetidin-2-one
  参考文献：
  名称：

  Ephedrine derived reusable chiral auxiliary for the synthesis of optically pure 3-hydroxy-4-aryl-β-lactams

  摘要：

  The diastereoselective synthesis of carious beta-lactams has been achieved using a chit-at acid auxiliary derived from (-)-ephedrine. An efficient acid-catalyzed cleavage of the chiral auxiliary from these beta-lactams to afford 3-hydroxy-4-aryl-cis-beta-lactams. which are precursors for analogues Of the taxol side chain, is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00039-9

文献信息

• Ephedrine derived reusable chiral auxiliary for the synthesis of optically pure 3-hydroxy-4-aryl-β-lactams
  作者：Bidhan A. Shinkre、Vedavati G. Puranik、B.M. Bhawal、A.R.A.S. Deshmukh

  DOI：10.1016/s0957-4166(03)00039-9

  日期：2003.2

  The diastereoselective synthesis of carious beta-lactams has been achieved using a chit-at acid auxiliary derived from (-)-ephedrine. An efficient acid-catalyzed cleavage of the chiral auxiliary from these beta-lactams to afford 3-hydroxy-4-aryl-cis-beta-lactams. which are precursors for analogues Of the taxol side chain, is described. (C) 2003 Elsevier Science Ltd. All rights reserved.