allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-bromopropanoate | 865701-96-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-bromopropanoate
• 英文别名: prop-2-enyl (2R)-3-bromo-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate
• CAS: 865701-96-8
• 化学式: C₂₁H₂₀BrNO₄
• 分子量: 430.298
• InChiKey: VMDGRUZOUYNLCR-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-bromopropanoate 在 四(三苯基膦)钯 吗啉 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-fluoren-9-ylmethoxycarbonyl-S-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-cysteine
  参考文献：
  名称：

  S-连接糖肽的一般策略。

  摘要：

  DOI：

  10.1002/anie.200500090
• 作为产物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以83%的产率得到allyl (R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-bromopropanoate
  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

• A General Strategy toward S-Linked Glycopeptides
  作者：Desiree A. Thayer、Henry N. Yu、M. Carmen Galan、Chi-Huey Wong

  DOI：10.1002/anie.200500090

  日期：2005.7.18
• 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.