tert-butyl (S)-4-azido-3-fluoromethyloxycarbamidobutyrate | 391624-33-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: tert-butyl (S)-4-azido-3-fluoromethyloxycarbamidobutyrate
• 英文别名: Fmoc-Asp(OtBu)-N3；tert-butyl (3S)-4-azido-3-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 391624-33-2
• 化学式: C₂₃H₂₆N₄O₄
• 分子量: 422.484
• InChiKey: FHGCWQZYOXLAEL-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-4-azido-3-fluoromethyloxycarbamidobutyrate 在 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 2.0h， 生成 (S)-3-(9-Fluorenylmethyloxycarbonyl)amino-4-azido-butanoic acid
  参考文献：
  名称：

  WO2007/41775

  摘要：

  公开号：
• 作为产物：
  描述：

  (3S)-3-[[(9H-芴-9-基甲氧基)羰基]氨基]-4-羟基-丁酸叔丁酯 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 以100%的产率得到tert-butyl (S)-4-azido-3-fluoromethyloxycarbamidobutyrate
  参考文献：
  名称：

  Solid-Phase Synthesis of Oligourea Peptidomimetics Employing the Fmoc Protection Strategy

  摘要：

  A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).

  DOI：

  10.1021/jo010656q

文献信息

• Efficient Synthesis of Glycosylated Asparaginic Acid Building Blocks via Click Chemistry
  作者：Thomas Ziegler、Nikolas Pietrzik、Carsten Schips

  DOI：10.1055/s-2008-1032150

  日期：2008.2

  4-tri- O-acetyl-6-azido-6-deoxy-1-thioglycosides (gluco, galacto, manno series), respectively (click chemistry). Thus obtained orthogonally protected L-asparaginic and ( S)-3-aminobutyric acids bearing an acetyl-protected glycose or glycoside moiety, linked through a triazole spacer, are suitable building blocks for combinatorial glycopeptide syntheses.

  铜催化 1完全乙酰化的炔丙基 1-硫糖苷（葡萄糖、半乳糖、甘露糖和鼠李糖系列）和 Fmoc-L-Asp(O-T-Bu)炔丙基酰胺与叔丁基 (S)-4-azido-3 的 ,3-偶极环加成-芴基甲氧基氨基丁酸、2,3,4,6-三-O-乙酰-糖基叠氮化物和乙基 2,3,4-三-O-乙酰-6-叠氮基-6-脱氧-1-硫糖苷（葡萄糖、半乳糖、甘露糖）系列），分别（点击化学）。由此获得的正交保护的L-天冬酰胺酸和(S)-3-氨基丁酸带有乙酰基保护的糖或糖苷部分，通过三唑间隔物连接，是组合糖肽合成的合适构件。
• Solid-Phase Synthesis of Azidomethylene Inhibitors Targeting Cysteine Proteases
  作者：Peng-Yu Yang、Hao Wu、Mei Yin Lee、Ashley Xu、Rajavel Srinivasan、Shao Q. Yao

  DOI：10.1021/ol800575z

  日期：2008.5.1

  An efficient strategy for the solid-phase synthesis of azidomethylene inhibitors targeting cysteine proteases is described. The method is highlighted by its compatibility with readily available building blocks, as well as its ability to accommodate different functional groups. A 249-member library has thus far been successfully synthesized, characterized, and screened against Caspase-1, -3 and -7.
• Solid phase synthesis of peptidotriazoles with multiple cycles of triazole formation
  作者：Zhongsheng Zhang、Erkang Fan

  DOI：10.1016/j.tetlet.2005.11.111

  日期：2006.1

  Peptidotriazoles, unnatural oligomers with alternating amide and triazole linkages, are synthesized efficiently on solid support. The key transformations involve multiple cycles of 1,2,3-triazolc formation, using soluble Cu(I) catalyst and conditions that do not generate precipitate on solid support nor require exclusion of oxygen. Our synthetic protocol will enable the preparation of other unnatural oligomers with multiple triazoles using solid phase methodologies. (c) 2005 Elsevier Ltd. All rights reserved.