prop-2-enyl 2-deuterio-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]sulfanylpropanoate | 1094039-36-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: prop-2-enyl 2-deuterio-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]sulfanylpropanoate
• CAS: 1094039-36-7
• 化学式: C₄₁H₅₂N₂O₈S
• 分子量: 733.931
• InChiKey: BRKHXEHLSIJUIK-RWGSIZHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  52.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  137.1
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  prop-2-enyl (2R)-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-methylsulfonyloxypropanoate 、 (R)-tert-butyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-mercaptopropanoate 在 四丁基溴化铵 、 重水 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以89%的产率得到prop-2-enyl 2-deuterio-2-[[1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutyl]amino]-3-[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]-3-oxopropyl]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.