allyl (S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-propanoate | 1094039-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: allyl (S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-propanoate
• 英文别名: prop-2-enyl (2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-tritylsulfanylpropanoate
• CAS: 1094039-28-7
• 化学式: C₃₈H₄₃NO₄S
• 分子量: 609.83
• InChiKey: ADRMWSPGCCSOCM-JGCGQSQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  44
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl (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70%的产率得到C₁₉H₂₉NO₄S
  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：

  (S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-propanoic acid 、 3-溴丙烯 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以92%的产率得到allyl (S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-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.