diphenylmethyl (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate | 171754-11-3

• 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: diphenylmethyl (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate
• CAS: 171754-11-3
• 化学式: C₂₃H₂₃NO₅
• 分子量: 393.439
• InChiKey: DXQONMQNUHIHKC-PXHWLCEJSA-N

物化性质

• 沸点：
  584.4±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  83.91
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  diphenylmethyl (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate 生成 diphenylmethyl (2R,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate
  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：

  (3S,4R)-3-((1R)-1-<(tert-butyldimethylsilyl)oxy>ethyl)-4-<(1S)-1-(formyl)ethyl>azetidin-2-one 在 吡啶 、 盐酸 、 甲烷磺酸 、 sodium methylate 、 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 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 diphenylmethyl (2S,4R,5R,6S)-6-<(1R)-1-hydroxyethyl>-4-methyl-3,7-dioxo-1-azabicyclo<3.2.0>heptan-2-carboxylate
  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。