(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone | 158150-46-0

• 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)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone
• 英文别名: benzhydryl (4R)-4-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidin-2-yl]-3-oxopentanoate
• CAS: 158150-46-0
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: MAFORPIDYBNGEJ-REABXYAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.17h， 生成 (3S,4R)-3-((1R)-1-hydroxyethyl)-4-((1R)-3-chloro-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl)-2-azetidinone
  参考文献：
  名称：

  Efficient and practical synthesis of 1⊝methylcarbapenems

  摘要：

  An efficient and practical method of synthesizing 1 beta-methylcarbapenem, S-4661, was developed. (4R)-4-[(1S)-1-Methylallyl]-2-azetidinone, 2, prepared stereoselectively from commercially available acetoxy-azetidinone 3, was converted to the beta-keto ester 6 in four steps. The iodonium ylide 5 was prepared from 6, then cyclized to obtain the bicyclic beta-keto ester 4. Finally, 4 was processed to the target product, S-4661, by conventional procedures. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01093-9
• 作为产物：
  描述：

  3-(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)-1-(2-甲氧基甲酰基噻吩-3-基)-磺酰脲 在 吡啶 、 盐酸 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 copper(ll) bromide 、 锌 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-3-diphenylmethoxycarbonyl-1-methyl-2-oxopropyl>-2-azetidinone
  参考文献：
  名称：

  Efficient and practical synthesis of 1⊝methylcarbapenems

  摘要：

  An efficient and practical method of synthesizing 1 beta-methylcarbapenem, S-4661, was developed. (4R)-4-[(1S)-1-Methylallyl]-2-azetidinone, 2, prepared stereoselectively from commercially available acetoxy-azetidinone 3, was converted to the beta-keto ester 6 in four steps. The iodonium ylide 5 was prepared from 6, then cyclized to obtain the bicyclic beta-keto ester 4. Finally, 4 was processed to the target product, S-4661, by conventional procedures. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01093-9

文献信息

• Novel and efficient synthesis of 1β-methylcarbapenems utilizing cyclization of hypervalent iodonium ylides
  作者：Masaharu Kume、Tadatoshi Kubota、Yasuyoshi Iso

  DOI：10.1016/0040-4039(95)01703-k

  日期：1995.10

  lβ-Methylcarbapenems were efficiently synthesized utilizing acid- and rhodium(II)-catalyzed cyclization of iodonium ylide intermediates, which were easily prepared from the corresponding β-keto ester derivatives.

  利用酸和铑（II）催化的碘化叶立德中间体中间体的环化反应，可以有效地合成1β-甲基咔啉，这些中间体很容易从相应的β-酮酯衍生物制备。
• Preparation of beta-lactam compounds, and intermediates therefor
  申请人：SHIONOGI & CO., LTD.

  公开号：EP0611115B1

  公开（公告）日：2001-04-18
• US5563264A
  申请人：——

  公开号：US5563264A

  公开（公告）日：1996-10-08
• US5580976A
  申请人：——

  公开号：US5580976A

  公开（公告）日：1996-12-03
• Efficient and practical synthesis of 1⊝methylcarbapenems
  作者：Masaharu Kume、Hiroaki Ooka、Hiroyuki Ishitobi

  DOI：10.1016/s0040-4020(96)01093-9

  日期：1997.2

  An efficient and practical method of synthesizing 1 beta-methylcarbapenem, S-4661, was developed. (4R)-4-[(1S)-1-Methylallyl]-2-azetidinone, 2, prepared stereoselectively from commercially available acetoxy-azetidinone 3, was converted to the beta-keto ester 6 in four steps. The iodonium ylide 5 was prepared from 6, then cyclized to obtain the bicyclic beta-keto ester 4. Finally, 4 was processed to the target product, S-4661, by conventional procedures. (C) 1997, Elsevier Science Ltd.