allyl (R)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-hydroxypropanoate | 1094039-26-5

• 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: allyl (R)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-hydroxypropanoate
• 英文别名: prop-2-enyl (2R)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-hydroxypropanoate
• CAS: 1094039-26-5
• 化学式: C₁₉H₂₉NO₅
• 分子量: 351.443
• InChiKey: LSZLMAFDOFEQMT-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  92.7
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl (R)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-hydroxypropanoate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以99%的产率得到prop-2-enyl (2R)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-methylsulfonyloxypropanoate
  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：

  N-(ivDde)-D-serine 、 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91%的产率得到allyl (R)-2-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)-3-hydroxypropanoate
  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.