allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-oxo-3-(2-(trimethylsilyl)ethoxy)propylthio)propanoate | 1094039-33-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-oxo-3-(2-(trimethylsilyl)ethoxy)propylthio)propanoate
• 英文别名: 2-trimethylsilylethyl (2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-oxo-3-prop-2-enoxypropyl]sulfanylpropanoate
• CAS: 1094039-33-4
• 化学式: C₄₂H₅₆N₂O₈SSi
• 分子量: 777.067
• InChiKey: ZRQLZMYGEZAFQE-GPOMZPHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.45
• 重原子数：
  54
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-oxo-3-(2-(trimethylsilyl)ethoxy)propylthio)propanoate 在 四(三苯基膦)钯 、 N-甲基苯胺 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.0h， 以87%的产率得到(2R)-3-[(2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-oxo-3-(2-trimethylsilylethoxy)propyl]sulfanyl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
  参考文献：
  名称：

  Concise Preparation of Tetra-orthogonally Protected (2S,6R)-Lanthionines

  摘要：

  Lantibiotics are antimicrobial peptides containing the unique bis-amino acids lanthionine and beta-methyllanthionine. While previous syntheses of lanthionine have often involved the coupling of precursors derived from D-serine and L-Cysteine, we here report an inverted strategy whereby D-cysteine and L-serine are employed as building blocks. This approach provides for a concise preparation of tetra-ortogonally protected (2R,6S)-lanthionines while allowing convenient introduction of orthogonal protecting groups not previously incorporated into lanthionines.

  DOI：

  10.1021/jo802415c
• 作为产物：
  描述：

  allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-bromopropanoate 、 2-trimethylsilylethyl (2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-sulfanylpropanoate 在 四丁基溴化铵 、 碳酸氢钠 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 14.0h， 以88%的产率得到allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-((S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-oxo-3-(2-(trimethylsilyl)ethoxy)propylthio)propanoate
  参考文献：
  名称：

  Concise Preparation of Tetra-orthogonally Protected (2S,6R)-Lanthionines

  摘要：

  Lantibiotics are antimicrobial peptides containing the unique bis-amino acids lanthionine and beta-methyllanthionine. While previous syntheses of lanthionine have often involved the coupling of precursors derived from D-serine and L-Cysteine, we here report an inverted strategy whereby D-cysteine and L-serine are employed as building blocks. This approach provides for a concise preparation of tetra-ortogonally protected (2R,6S)-lanthionines while allowing convenient introduction of orthogonal protecting groups not previously incorporated into lanthionines.

  DOI：

  10.1021/jo802415c

文献信息

• Concise Preparation of Tetra-orthogonally Protected (2<i>S</i>,6<i>R</i>)-Lanthionines
  作者：Nathaniel I. Martin

  DOI：10.1021/jo802415c

  日期：2009.1.16

  Lantibiotics are antimicrobial peptides containing the unique bis-amino acids lanthionine and beta-methyllanthionine. While previous syntheses of lanthionine have often involved the coupling of precursors derived from D-serine and L-Cysteine, we here report an inverted strategy whereby D-cysteine and L-serine are employed as building blocks. This approach provides for a concise preparation of tetra-ortogonally protected (2R,6S)-lanthionines while allowing convenient introduction of orthogonal protecting groups not previously incorporated into lanthionines.