(E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester | 186021-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester
• 英文别名: phenacyl 3-[2-[2-[2-[(E)-4-bromobut-2-enoxy]ethoxy]ethoxy]ethoxy]propanoate
• CAS: 186021-07-8
• 化学式: C₂₁H₂₉BrO₇
• 分子量: 473.361
• InChiKey: QWNZEIYFIZCIHZ-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester 在 四丁基溴化铵 、 碳酸氢钠 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid
  参考文献：
  名称：

  HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides

  摘要：

  The recently developed allylic HYCRON anchor(1) exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(O)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-alpha GalNAc-(T-N)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.

  DOI：

  10.1021/jo960743w
• 作为产物：
  描述：

  (E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid tert-butyl ester 在 potassium fluoride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester
  参考文献：
  名称：

  HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides

  摘要：

  The recently developed allylic HYCRON anchor(1) exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(O)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-alpha GalNAc-(T-N)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.

  DOI：

  10.1021/jo960743w

文献信息

• Convergent Strategies for the Attachment of Fluorescing Reporter Groups to Peptide Nucleic Acids in Solution and on Solid Phase
  作者：Oliver Seitz、Olaf Köhler

  DOI：10.1002/1521-3765(20010917)7:18<3911::aid-chem3911>3.0.co;2-1

  日期：2001.9.17

  The site-selective conjugation of peptide nucleic acids (PNA) with fluorescent reporter groups is essential for the construction of hybridisation probes that can report the presence of a particular DNA sequence. This paper describes convergent methods for the solution- and solid-phase synthesis of multiply labelled PNA oligomers. The solid-phase synthesis of protected PNA enabled the selective attachment

  肽核酸（PNA）与荧光报告基团的位点选择性缀合对于构建可报告特定DNA序列存在的杂交探针至关重要。本文介绍了收敛方法，用于固相合成多标记的PNA低聚物。受保护的PNA的固相合成使得荧光标记能够选择性地附着在C末端（DNA中的3'），这表明进一步操作受保护的PNA片段是可行的。为了与内部位点缀合，引入了一种方法，该方法允许在树脂上组装改性单体，从而无需在溶液中合成整个单体。此外，结果表明，将高度正交的保护基策略与化学选择性缀合反应结合使用，可以快速，自动地进行固相合成双标记PNA探针。通过利用适当附加的荧光团之间的荧光共振能量转移（FRET），可以实时测量核酸杂交。与基于DNA的分子信标类似，双重标记的PNA探针仅在单链状态下发出弱荧光。然而，与互补寡核苷酸的杂交诱导了结构重组并赋予了生动的荧光增强。通过利用适当附加的荧光团之间的荧光共振能量转移（FRET），可以实时测量核酸杂交。类似于基于
• A Convergent Strategy for the Modification of Peptide Nucleic Acids: Novel Mismatch-Specific PNA-Hybridization Probes
  作者：Oliver Seitz、Frank Bergmann、Dieter Heindl

  DOI：10.1002/(sici)1521-3773(19990802)38:15<2203::aid-anie2203>3.0.co;2-2

  日期：1999.8.2

  Coupling of nonnatural nucleobases to the orthogonally protected backbone 1 on the solid phase provided access to novel peptide nucleic acid (PNA) conjugates 2, which are difficult to synthesize by standard routes. Hybridization probes containing the thiazolorange dye might allow DNA sequence analysis in real time. B-CH(2)CO=modified nucleobase, fluorescent dye, etc; Boc, Fmoc=protecting groups.
• HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides
  作者：Oliver Seitz、Horst Kunz

  DOI：10.1021/jo960743w

  日期：1997.2.1

  The recently developed allylic HYCRON anchor(1) exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(O)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-alpha GalNAc-(T-N)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.