(3R,4S)-1-benzyl-4-[(4S,5S)-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxyazetidin-2-one | 260354-47-0

• 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: (3R,4S)-1-benzyl-4-[(4S,5S)-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxyazetidin-2-one
• CAS: 260354-47-0
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: DFESRPYFHKFVED-YIPNQBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-benzyl-4-[(4S,5S)-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxyazetidin-2-one 在 palladium on activated charcoal 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 氢气 、 potassium bromide 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 (4S)-3-benzyl-4-[(4S,5S)-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1,3-oxazolidine-2,5-dione
  参考文献：
  名称：

  A Strategy for the Asymmetric Aminohomologation of α,β-Dihydroxy Aldehydes:  Application to the Synthesis of the Southwest Tripeptide Segment of Echinocandin B

  摘要：

  The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic acid methyl ester, a completely diastereoselective [2 + 2] hydroxyketene-imine cycloaddition, and the TEMPO-assisted cyclo-expansion of the resulting 3-hydroxy beta-lactam to the corresponding alpha-amino acid N-carboxy anhydride (NCA). The smooth opening of the latter upon treatment with L-Thr((OSiBuPh2)-Bu-t)OMe and further acylation with the N-Cbz protected L-4-tert-butyldiphenylsilyloxy proline rendered the southwest portion of echinocandin B.

  DOI：

  10.1021/jo990964c
• 作为产物：
  描述：

  methyl (2-RS,3-SR)-2,3-dihydroxy-3-(methoxyphenyl)propanoate 在 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 、 苯 为溶剂， 反应 4.0h， 生成 (3R,4S)-1-benzyl-4-[(4S,5S)-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxyazetidin-2-one
  参考文献：
  名称：

  A Strategy for the Asymmetric Aminohomologation of α,β-Dihydroxy Aldehydes:  Application to the Synthesis of the Southwest Tripeptide Segment of Echinocandin B

  摘要：

  The synthesis of the (2S,3S,4S)-3,4-dihydroxyhomotyrosine amino acid segment, present in echinocandin B, in its activated form ready for peptide coupling is described. The key steps of the approach are the enantioselective AD reaction of 4-methoxycinnamic acid methyl ester, a completely diastereoselective [2 + 2] hydroxyketene-imine cycloaddition, and the TEMPO-assisted cyclo-expansion of the resulting 3-hydroxy beta-lactam to the corresponding alpha-amino acid N-carboxy anhydride (NCA). The smooth opening of the latter upon treatment with L-Thr((OSiBuPh2)-Bu-t)OMe and further acylation with the N-Cbz protected L-4-tert-butyldiphenylsilyloxy proline rendered the southwest portion of echinocandin B.

  DOI：

  10.1021/jo990964c