(3R,4S)-1-benzyl-4-[(1S,2S)-1,2-dihydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylmethoxyazetidin-2-one | 260354-44-7

• 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-[(1S,2S)-1,2-dihydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylmethoxyazetidin-2-one
• CAS: 260354-44-7
• 化学式: C₂₆H₂₇NO₅
• 分子量: 433.504
• InChiKey: FJQOWJFODSNCRJ-OJJQZRKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-benzyl-4-[(1S,2S)-1,2-dihydroxy-2-(4-methoxyphenyl)ethyl]-3-phenylmethoxyazetidin-2-one 在 sodium periodate 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到(+)-(3R,4R)-cis-1-benzyl-3-benzyloxy-4-formyl-2-azetidinone
  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：

  Benzyl-[1-[(4S,5S)-5-(4-methoxy-phenyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-meth-(E)-ylidene]-amine 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (3R,4S)-1-benzyl-4-[(1S,2S)-1,2-dihydroxy-2-(4-methoxyphenyl)ethyl]-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

文献信息

• A β-Lactam-Based Stereoselective Access to β,γ-Dihydroxy α-Amino Acid-Derived Peptides with Either α,β-Like or Unlike Configurations
  作者：Claudio Palomo、Mikel Oiarbide、Aitor Landa、Aitor Esnal、Anthony Linden

  DOI：10.1021/jo001786m

  日期：2001.6.1

  A concise access to alpha,beta-dihydroxy alpha-amino acid-derived N-carboxy anhydrides (NCAs) with either like or unlike relative configuration is described. The key steps of the synthetic route are the preparation of the nonracemic 4-alkenyl beta-lactams, through either Horner-type olefination of a common 4-formyl beta-lactam or the Corey-Winter alkene synthesis applied to 4-dihydroxyalkyl beta-lactams

  简述了获得具有相似或不同相对构型的α，β-二羟基α-氨基酸衍生的N-羧酸酐（NCA）的方法。合成路线的关键步骤是通过普通的4-甲酰基β-内酰胺的霍纳型烯化反应或用于4-二羟基烷基β-内酰胺的Corey-Winter烯烃合成制备非外消旋的4-烯基β-内酰胺。 ，然后进行Sharpless AD反应，随后TEMPO促进了相应的4-取代的3-羟基β-内酰胺的扩环。还已经在各种反应条件下研究了用不同的O-和N-亲核试剂，包括导致肽的α-氨基酯处理，由此制备的NCA的打开。