2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-pentanoic acid tert-butyl ester | 290292-98-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-pentanoic acid tert-butyl ester
• CAS: 290292-98-7
• 化学式: C₂₄H₂₉NO₅
• 分子量: 411.498
• InChiKey: QJQLXYXSDCIVNU-NRFANRHFSA-N

物化性质

• 沸点：
  585.6±50.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-pentanoic acid tert-butyl ester 在 咪唑 、 碘 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 tert-butyl (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpentanoate
  参考文献：
  名称：

  Straightforward Entry to S-Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics

  摘要：

  Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohydrate acetates in a few steps. Mild basic conditions make the conjugation reaction compatible with Fmoc-iodo-amino acids. To validate the strategy the glycosylated building blocks were used for SPPS and the unprecedented incorporation of a long thio-oligosaccharide to the peptide chain was demonstrated.

  DOI：

  10.1021/ol503664t
• 作为产物：
  描述：

  (S)-5-Ethoxycarbonyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-pentanoic acid tert-butyl ester 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以800 mg的产率得到2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-hydroxy-pentanoic acid tert-butyl ester
  参考文献：
  名称：

  Solid-Phase Synthesis of New S-Glycoamino Acid Building Blocks

  摘要：

  [GRAPHICS]Efficient synthesis of unprotected S-glycoamino acid building blocks in the solid phase by coupling a sugar 1-thiolate with iodine activated fluoren-9-ylmethoxycarbonyl (Fmoc) protected amino acids.

  DOI：

  10.1021/ol006019o

文献信息

• Chemoselective derivitization of folded synthetic insulin variants with potassium acyltrifluoroborates (KATs)
  作者：Gabor N. Boross、Dominik Schauenburg、Jeffrey W. Bode

  DOI：10.1002/hlca.201800214

  日期：——

  pattern and allows facile incorporation at the B0 position of Glargine M2 of a new ornithine hydroxylamine protected with a photolabile group. The folded insulin is readily modified by photo‐deprotection followed by amide‐forming KAT ligation to give insulin variants labeled with dyes, lipids, and PEGs, as well as the formation of a covalent dimer.

  含有鸟氨酸-羟胺残基的合成折叠胰岛素变异体可通过与酰基三氟硼酸钾（KAT）形成酰胺连接，在水性缓冲液中轻松修饰。合成胰岛素类似物是通过Fmoc-SPPS，α-酮酸-羟胺（KAHA）连接和人工C肽制备的，该C肽可提供正确的二硫键模式，并易于在新鸟氨酸羟胺的Gg精氨酸M2的B0位置掺入。与不稳定的组。折叠的胰岛素很容易通过光脱保护，然后进行酰胺形成的KAT连接来修饰，从而得到用染料，脂质和PEG标记的胰岛素变体，并形成共价二聚体。