2-trimethylsilylethyl (2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-sulfanylpropanoate | 1094039-31-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-trimethylsilylethyl (2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-sulfanylpropanoate
• CAS: 1094039-31-2
• 化学式: C₂₁H₃₇NO₄SSi
• 分子量: 427.681
• InChiKey: OJYZBVDMMWTPHZ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl (S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-propanoate 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到2-trimethylsilylethyl (2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-sulfanylpropanoate
  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.