3-azidopropyl 3,6-di-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azidopropyl 3,6-di-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside
• 英文别名: 3-azidopropyl 3,6-di-O-di-tert-butyldimethylsilyl-α-D-mannopyranoside；(2S,3S,4S,5R,6R)-2-(3-azidopropoxy)-4-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]oxane-3,5-diol
• 化学式: C₂₁H₄₅N₃O₆Si₂
• 分子量: 491.776
• InChiKey: BFYMLRKLMRBYOR-GFEQUFNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-azidopropyl 3,6-di-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside 在 sodium hydride 、 氟化氢吡啶 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 3-azidopropyl 2,4-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Combating DC‐SIGN‐mediated SARS‐CoV‐2 dissemination by glycan‐mimicking polymers

  摘要：

  摘要 许多病毒利用人类 C 型凝集素受体树突状细胞特异性 ICAM-3 抓取非整合素（DC-SIGN）进入细胞并传播病毒。因此，通过糖源配体抑制 DC-SIGN 介导的病毒附着已成为广谱抗病毒疗法的一种有前途的策略。在本文中，我们评估了接枝到聚赖氨酸支架上的低聚甘露糖和复合型聚糖的几种同源片段作为多价 DC-SIGN 配体。所选碳水化合物表位的范围包括线性（α- d-Man-(1→2)-α- d-Man，α- d-Man-(1→2)-α- d-Man-(1→2)-α- d-Man-(1→3)-α- d-Man）和支化（α- d-Man-(1→6)-[α- d-Man-(1→3)]-α- d-Man）低聚甘露糖苷以及α- l-Fuc。研究了单价和多价结合的热力学，以揭示与四价受体相互作用的分子细节。病毒附着和 DC-SIGN 介导的病毒传播的细胞模型显示，所展示的糖聚合物分别在低皮摩尔和纳摩尔范围内具有很高的效力。低聚甘露糖表位的高活性与聚 l-lysine 支架的生物相容性，凸显了进一步临床前开发多价 DC-SIGN 配体的潜力。

  DOI：

  10.1002/ardp.202300396
• 作为产物：
  描述：

  D-甘露糖 在 咪唑 、 sodium azide 、 silica gel supported sulfuric acid 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 3-azidopropyl 3,6-di-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of unsymmetrical 3,6-branched Man5 oligosaccharide: a comparison between one-pot sequential glycosylation and stepwise synthesis

  摘要：

  An expeditious three-component, one-pot sequential glycosylation protocol has been developed for the preparation of 3,6-branched unsymmetrical mannopentaose (Man5), employing a mannose trisaccharide donor, a mannose monosaccharide donor and a mannose monosaccharide acceptor. The high efficiency of this one-pot procedure was demonstrated by comparison study with a stepwise synthesis using the same three building blocks. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.09.010

文献信息

• Synthesis of Branched Man5 Oligosaccharides and an Unusual Stereochemical Observation
  作者：Nardos Teumelsan、Xuefei Huang

  DOI：10.1021/jo7013824

  日期：2007.11.1

  [GRAPHICS]Branched mannopentaoses, were synthesized through two routes. While assembly from the nonreducing end to the reducing end was more convergent with fewer intermediate steps, two diastereomers were obtained. On the other hand, synthesis from the reducing end to the nonreducing end yielded the mannopentaose with the desired stereochemistry as a single isomer. Our results suggest that it is still challenging to reliably predict stereochemical outcome of a glycosylation reaction. It is necessary to thoroughly characterize anomeric configurations of newly formed glycosidic linkages in complex oligosaccharide synthesis.
• Synthesis of unsymmetrical 3,6-branched Man5 oligosaccharide: a comparison between one-pot sequential glycosylation and stepwise synthesis
  作者：Yan Zhang、Congcong Chen、Lan Jin、Haining Tan、Fengshan Wang、Hongzhi Cao

  DOI：10.1016/j.carres.2014.09.010

  日期：2015.1

  An expeditious three-component, one-pot sequential glycosylation protocol has been developed for the preparation of 3,6-branched unsymmetrical mannopentaose (Man5), employing a mannose trisaccharide donor, a mannose monosaccharide donor and a mannose monosaccharide acceptor. The high efficiency of this one-pot procedure was demonstrated by comparison study with a stepwise synthesis using the same three building blocks. (C) 2014 Elsevier Ltd. All rights reserved.
• Combating DC‐SIGN‐mediated SARS‐CoV‐2 dissemination by glycan‐mimicking polymers
  作者：Jonathan Cramer、Xiaohua Jiang、Butrint Aliu、Beat Ernst

  DOI：10.1002/ardp.202300396

  日期：2024.4

  Many viruses exploit the human C‐type lectin receptor dendritic cell‐specific ICAM‐3 grabbing nonintegrin (DC‐SIGN) for cell entry and virus dissemination. An inhibition of DC‐SIGN‐mediated virus attachment by glycan‐derived ligands has, thus, emerged as a promising strategy toward broad‐spectrum antiviral therapeutics. In this contribution, several cognate fragments of oligomannose‐ and complex‐type glycans grafted onto a poly‐l‐lysine scaffold are evaluated as polyvalent DC‐SIGN ligands. The range of selected carbohydrate epitopes encompasses linear (α‐ d‐Man‐(1→2)‐α‐ d‐Man, α‐ d‐Man‐(1→2)‐α‐ d‐Man‐(1→2)‐α‐ d‐Man‐(1→3)‐α‐ d‐Man) and branched (α‐ d‐Man‐(1→6)‐[α‐ d‐Man‐(1→3)]‐α‐ d‐Man) oligomannosides, as well as α‐ l‐Fuc. The thermodynamics of binding are investigated on a mono‐ and multivalent level to shed light on the molecular details of the interactions with the tetravalent receptor. Cellular models of virus attachment and DC‐SIGN‐mediated virus dissemination reveal a high potency of the presented glycopolymers in the low pico‐ and nanomolar ranges, respectively. The high activity of oligomannose epitopes in combination with the biocompatible properties of the poly‐ l‐lysine scaffold highlights the potential for further preclinical development of polyvalent DC‐SIGN ligands.

  摘要 许多病毒利用人类 C 型凝集素受体树突状细胞特异性 ICAM-3 抓取非整合素（DC-SIGN）进入细胞并传播病毒。因此，通过糖源配体抑制 DC-SIGN 介导的病毒附着已成为广谱抗病毒疗法的一种有前途的策略。在本文中，我们评估了接枝到聚赖氨酸支架上的低聚甘露糖和复合型聚糖的几种同源片段作为多价 DC-SIGN 配体。所选碳水化合物表位的范围包括线性（α- d-Man-(1→2)-α- d-Man，α- d-Man-(1→2)-α- d-Man-(1→2)-α- d-Man-(1→3)-α- d-Man）和支化（α- d-Man-(1→6)-[α- d-Man-(1→3)]-α- d-Man）低聚甘露糖苷以及α- l-Fuc。研究了单价和多价结合的热力学，以揭示与四价受体相互作用的分子细节。病毒附着和 DC-SIGN 介导的病毒传播的细胞模型显示，所展示的糖聚合物分别在低皮摩尔和纳摩尔范围内具有很高的效力。低聚甘露糖表位的高活性与聚 l-lysine 支架的生物相容性，凸显了进一步临床前开发多价 DC-SIGN 配体的潜力。