5-(benzyloxycarbonylamino)pentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside | 441775-35-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(benzyloxycarbonylamino)pentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-[5-(phenylmethoxycarbonylamino)pentoxy]oxan-2-yl]methyl acetate
• CAS: 441775-35-5
• 化学式: C₂₇H₃₇NO₁₂
• 分子量: 567.59
• InChiKey: SNYKNMIBRZNLSD-JMTTVTNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  40
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  162
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-(benzyloxycarbonylamino)pentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 溶剂黄146 、 乙酸乙酯 为溶剂， 20.0~25.0 ℃ 、100.0 kPa 条件下， 反应 3.0h， 生成
  参考文献：
  名称：

  Preparation of glycosyl amino acids as building blocks for the combinatorial synthesis of neoglycoconjugates

  摘要：

  Several neoglycosyl amino acids possessing a sugar residue, a spacer and trifunctional amino acid moiety were synthesized both in solution and solid phase by activating the carboxylic group as its pentafluorophenyl ester for condensation. The methodology is useful for application in combinatorial syntheses of neoglycoconjugates as potential mimics for oligosaccharides. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00212-4
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 、 5-(Z-氨基)-1-戊醇 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以59%的产率得到5-(benzyloxycarbonylamino)pentyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
  参考文献：
  名称：

  Analysis of the dispersity in carbohydrate loading of synthetic glycoproteins using MALDI-TOF mass spectrometry

  摘要：

  质量光谱峰展宽与蛋白质偶联反应中产物分散度的统计相关性，有助于更详细地表征潜在治疗性偶联物。

  DOI：

  10.1039/c0cc03420g

文献信息

• VaporSPOT: Parallel Synthesis of Oligosaccharides on Membranes
  作者：Alexandra Tsouka、Pietro Dallabernardina、Marco Mende、Eric T. Sletten、Sabrina Leichnitz、Klaus Bienert、Kim Le Mai Hoang、Peter H. Seeberger、Felix F. Loeffler

  DOI：10.1021/jacs.2c07285

  日期：2022.11.2

  Automated chemical synthesis has revolutionized synthetic access to biopolymers in terms of simplicity and speed. While automated oligosaccharide synthesis has become faster and more versatile, the parallel synthesis of oligosaccharides is not yet possible. Here, a chemical vapor glycosylation strategy (VaporSPOT) is described that enables the simultaneous synthesis of oligosaccharides on a cellulose membrane

  自动化化学合成在简单性和速度方面彻底改变了生物聚合物的合成途径。虽然自动化低聚糖合成变得更快和更通用，但寡糖的平行合成尚不可能。在这里，描述了一种化学气相糖基化策略 (VaporSPOT)，它能够在纤维素膜固体支持物上同时合成低聚糖。不同的接头允许对目标寡糖进行灵活和直接的切割、纯化和表征。该方法是开发并行自动聚糖合成平台的基础。
• Efficient Preparation of Glycoclusters from Silsesquioxanes
  作者：Yongjun Gao、Atsuko Eguchi、Kazuaki Kakehi、Yuan C. Lee

  DOI：10.1021/ol040043a

  日期：2004.9.1

  A new type of glycocluster based on polyhedral oligosilsesquioxanes (POSS) has been efficiently prepared from unprotected mannoside and lactoside employing a convergent approach of thiol-radical addition reaction. The versatility of this approach was demonstrated by functionalization of mannosides and lactosides of different-length spacers.
• Chain-growth polyglycosylation: synthesis of linker-equipped mannosyl oligomers
  作者：Heiko J. Schuster、Balakumar Vijayakrishnan、Benjamin G. Davis

  DOI：10.1016/j.carres.2014.06.021

  日期：2015.2

  Direct syntheses of acetylated poly-mannosides can be achieved in one-step starting from a fully acetylated thioglycoside mannosyl donor using a polymerization-type strategy under the correct conditions. Under conditions that allow polymer growth from non-reducing to reducing end (N -> R), different acceptor alcohols can be used as the 'terminating acceptors' to install different linkers at the reducing terminus. The efficiency is dependent on substituents of the linker, its length, temperature and choice of Lewis acid activator. (C) 2014 The Authors. Published by Elsevier Ltd.