(S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-propanoic acid | 1094039-27-6

• 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: (S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-propanoic acid
• 英文别名: (2S)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-tritylsulfanylpropanoic acid
• CAS: 1094039-27-6
• 化学式: C₃₅H₃₉NO₄S
• 分子量: 569.765
• InChiKey: GDYMXHPLYTWNOE-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  83.47
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(三甲硅基)乙醇 、 (S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-propanoic acid 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以92%的产率得到2-(trimethylsilyl)ethyl (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
• 作为产物：
  描述：

  2-isovaleryldimedone 、 S-trityl-D-cysteine 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以95%的产率得到(S)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-(tritylthio)-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

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.