cis-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-phenylazetidin-2-one

• 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: cis-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-phenylazetidin-2-one
• 英文别名: cis-1-(t-butoxycarbonyl)-3-triethylsiloxy-4-phenylazetidin-2-one；(3S,4R)-tert-Butyl 2-oxo-4-phenyl-3-((triethylsilyl)oxy)azetidine-1-carboxylate；tert-butyl (3S,4R)-2-oxo-4-phenyl-3-triethylsilyloxyazetidine-1-carboxylate
• 化学式: C₂₀H₃₁NO₄Si
• 分子量: 377.556
• InChiKey: LHTDXUKSFSMGCA-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-phenylazetidin-2-one 、 7,10-二[O-(三乙基硅烷基)]-10-去乙酰基浆果赤霉素III 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 2',7,10-tris-triethylsilyl taxotere
  参考文献：
  名称：

  Beta-Lactams useful for preparation of substituted isoserine esters using metal alkoxides

  摘要：

  公开号：

  EP1193252B1
• 作为产物：
  描述：

  (+/-)-cis-3-acetoxy-1-(4-methoxyphenyl)-4-phenyl-2-azetidinone 在 4-二甲氨基吡啶 、 lithium hydroxide 、 ammonium cerium(IV) nitrate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 10.0h， 生成 cis-1-(tert-butoxycarbonyl)-3-triethylsilyloxy-4-phenylazetidin-2-one
  参考文献：
  名称：

  Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-O-Triethylsilylbaccatin III

  摘要：

  The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.

  DOI：

  10.1021/jo061339s

文献信息

• C2 substituted phenyl taxane derivatives and pharmaceutical compositions containing them
  申请人：Florida State University

  公开号：US06339164B1

  公开（公告）日：2002-01-15

  Taxane derivatives having alternative C2 substituents.

  具有替代C2取代基的紫杉烷衍生物。
• EP1980562
  申请人：——

  公开号：——

  公开（公告）日：——
• Beta-Lactams useful for preparation of substituted isoserine esters using metal alkoxides
  申请人：FLORIDA STATE UNIVERSITY

  公开号：EP1193252B1

  公开（公告）日：2006-12-27
• Synthesis of Docetaxel and Butitaxel Analogues through Kinetic Resolution of Racemic β-Lactams with 7-<i>O</i>-Triethylsilylbaccatin III
  作者：Haibo Ge、Jared T. Spletstoser、Yan Yang、Margaret Kayser、Gunda I. Georg

  DOI：10.1021/jo061339s

  日期：2007.2.1

  The kinetic resolution of racemic cis-4-phenyl- and cis-4-tert-butyl-3-hydroxy-beta-lactam derivatives with 7-O-triethylsilylbaccatin III yielded paclitaxel and butitaxel analogues with high diastereoselectivity. The results demonstrated that the tert-butyldimethylsilyl protecting group at the C3-hydroxy group of the beta-lactams provided optimum kinetic resolution in comparison with the sterically less demanding triethylsilyl group and the larger triisopropylsilyl group. In addition, it was found that the C4 beta-lactam substituents also influenced diastereoselectivity. The C4 tert-butyl-beta-lactams provided better diastereoselectivity than the corresponding C4 phenyl beta-lactams.