N^α-fluoren-9-ylmethoxycarbonyl-N^γ-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-asparagine tert-butyl ester | 467465-72-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: N^α-fluoren-9-ylmethoxycarbonyl-N^γ-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-asparagine tert-butyl ester
• 英文别名: Fmoc-Asn[Gal(OAc)4]-O-tBu；N²-[(9H-fluoren-9-ylmethoxy)carbonyl]-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-asparagine tert-butyl ester；Fmoc-L-Asn(GalAc4)-Ot-Bu；tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxo-4-[[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]butanoate
• CAS: 467465-72-1
• 化学式: C₃₇H₄₄N₂O₁₄
• 分子量: 740.761
• InChiKey: UUDIZJIPQWEEJY-WIEVSHRFSA-N

物化性质

• 沸点：
  843.9±65.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  208
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  N^α-fluoren-9-ylmethoxycarbonyl-N^γ-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-asparagine tert-butyl ester 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到N^α-fluoren-9-ylmethoxycarbonyl-N^γ-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-asparagine
  参考文献：
  名称：

  A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides

  摘要：

  本研究提出了一条便捷且产率高的制备多个Boc和Fmoc保护的N-连接糖肽单体的方法。这些构建单元可用于糖肽或糖肽模拟物的固相合成，通过制备N-连接的十二糖肽Ac–(GlyProAsn[Gal])4–NH2为例，展示了其作为潜在胶原蛋白模拟物的应用。

  DOI：

  10.1039/b201296k
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 palladium on activated charcoal 吡啶 、 叠氮基三甲基硅烷 、 四丁基氟化铵 、 氢溴酸 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 N^α-fluoren-9-ylmethoxycarbonyl-N^γ-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-L-asparagine tert-butyl ester
  参考文献：
  名称：

  A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides

  摘要：

  本研究提出了一条便捷且产率高的制备多个Boc和Fmoc保护的N-连接糖肽单体的方法。这些构建单元可用于糖肽或糖肽模拟物的固相合成，通过制备N-连接的十二糖肽Ac–(GlyProAsn[Gal])4–NH2为例，展示了其作为潜在胶原蛋白模拟物的应用。

  DOI：

  10.1039/b201296k

文献信息

• Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations
  作者：Laura Sršan、Thomas Ziegler

  DOI：10.3762/bjoc.16.80

  日期：——

  disaccharides containing glycopeptides were prepared in solution. The applicability of two common peptide coupling reagents, using an orthogonal Fmoc/t-Bu strategy along with acetyl protecting groups for the carbohydrate moiety, was studied. Thus, the prepared libraries of glycopeptides were designed as model systems of cell surfaces for future investigations by combined preparative mass spectroscopy and

  为了研究寡糖和拟肽的生物学功能，在溶液中制备了新的含有糖肽的天冬酰胺基单糖和二糖。使用正交的Fmoc / t- Bu策略以及碳水化合物部分的乙酰基保护基，研究了两种常见的肽偶联剂的适用性。因此，将制备的糖肽文库设计为细胞表面的模型系统，以供将来通过在金属表面上使用软着陆电喷雾束沉积（ES-IBD）的组合制备质谱和扫描隧道显微镜（STM）进行研究。
• Microwave-assisted reaction of glycosylamine with aspartic acid
  作者：Feliciana Real-Fernández、Francesca Nuti、M. Angeles Bonache、Marco Boccalini、Stefano Chimichi、Mario Chelli、Anna Maria Papini

  DOI：10.1007/s00726-010-0484-8

  日期：2010.7

  The synthesis of N-protected glycosyl amino acids from amines has been investigated and it was found that, under microwave conditions, glycosylamines could be hydrolyzed leading to new products containing a glycosyl ester linkage. The efficiency of the microwave-induced glycosylation of aspartic acid was studied comparing the microwave activity between amide and ester bond formation. Different sugar

  已经研究了由胺合成N-保护的糖基氨基酸，并且发现在微波条件下，糖基胺可以被水解，从而产生含有糖基酯键的新产物。比较了酰胺和酯键形成之间的微波活性，研究了微波诱导的天冬氨酸糖基化的效率。已经采用了不同的糖部分来证明简单和可再现的偶联方法。通过NMR光谱进一步表征了新的糖基酯化合物。
• A convenient microwave-assisted synthesis of N-glycosyl amino acids
  作者：Ilaria Paolini、Francesca Nuti、Maria de la Cruz Pozo-Carrero、Francesca Barbetti、Beata Kolesinska、Zbigniew J. Kaminski、Mario Chelli、Anna M. Papini

  DOI：10.1016/j.tetlet.2007.02.087

  日期：2007.4

  Optimization of coupling reactions of glycosylamines with Fmoc-protected aspartic acid, by microwave approach, is described. Different reaction conditions, quantities of substrates and solvents were tested to develop simple and reproducible methodologies. The best results were obtained using new triazine-based coupling reagents with a monomode microwave Discover (R) BenchMate (TM) instrument (CEM). The N-glycosyl amino acids were then deprotected to achieve final products for SPPS. (c) 2007 Elsevier Ltd. All rights reserved.
• Preparation of S‐ and N‐Linked Glycosylated Amino Acid Building Blocks for Solid‐phase Glycopeptide Library Synthesis*
  作者：C. Maljaars、Koen Halkes、Wim de Oude、Seléne van der Poel、Niels Pijnenburg、Johannis Kamerling

  DOI：10.1081/car-200066915

  日期：2005.8.1

  A general route for the preparation of 1,2-trans-linked S-glycosylated amino acid building blocks by a Lewis-acid-promoted condensation of peracetylated glycosyl donors and N-alpha-Fmoc-Cys-OH, in good overall yield, is described. In addition, a short and time-efficient route was applied for the synthesis of N-glycosylated amino acid building blocks in good overall yields by coupling unprotected glycosylamines and N-alpha-Fmoc-Asp(OH)-(OBu)-Bu-t using TBTU activation.