methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 195875-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]Man2Ac(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Man1Me；[(2S,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 195875-44-6
• 化学式: C₅₇H₆₂O₁₂
• 分子量: 939.112
• InChiKey: LJCMHABAMJOXSX-ISJKUCFXSA-N

物化性质

• 沸点：
  927.1±65.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  69
• 可旋转键数：
  25
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 sodium methylate 、 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以77%的产率得到甲基 6-O-alpha-D-甘露糖基-alpha-D-吡喃甘露糖苷
  参考文献：
  名称：

  Synthesis and binding affinity analysis of α1-2- and α1-6- O / S -linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

  摘要：

  The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.09.015
• 作为产物：
  描述：

  3,4,6-三-O-苄基-beta-D-吡喃甘露糖-1,2-(甲基原乙酸酯) 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.75h， 生成 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis and binding affinity analysis of α1-2- and α1-6- O / S -linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

  摘要：

  The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards alpha 1-2- and alpha 1-6-linked dimannosides with S-or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrenemediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the alpha 1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the alpha 1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the alpha 1-2-analog displayed very similar binding compared to the O-linked structure. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2017.09.015

文献信息

• Synthesis and structural investigation of a series of mannose-containing oligosaccharides using mass spectrometry
  作者：S. Daikoku、R. Pendrill、Y. Kanie、Y. Ito、G. Widmalm、O. Kanie

  DOI：10.1039/c7ob02723k

  日期：——

  mass spectrometry (ERMS), and 1H nuclear magnetic resonance spectroscopy. The CID experiments of sodiated species of disaccharides and ERMS experiments revealed that the order of stability of mannosyl linkages was as follows: 6-linked > 4-linked ≧ 2-linked > 3-linked mannosyl residues. Analysis of linear trisaccharides revealed that the order observed in disaccharides could be applied to higher glycans

  使用碰撞诱导解离（CID），能量分辨质谱（ERMS）和1制备了一系列与由α-甘露糖苷组成的与天然存在的和生物学上相关的聚糖相关的化合物H核磁共振波谱学。二糖的糖化物种类的CID实验和ERMS实验显示，甘露糖基键的稳定性的顺序如下：6-连接的> 4-连接的≥2-连接的> 3-连接的甘露糖基残基。线性三糖的分析表明，在二糖中观察到的顺序可以应用于更高的聚糖。支链的三糖显示出明显的解离模式，具有两个构成的二糖离子。使用二糖光谱可以估算该离子混合物的含量。支链三糖中3-位和6-位甘露糖键的水解显示3-键的断裂速度是6-键的两倍。观察到溶液相水解和气相解离具有相似的能量。
• Microreactor-based reaction optimization in organic chemistry—glycosylation as a challenge
  作者：Daniel M. Ratner、Edward R. Murphy、Manish Jhunjhunwala、Daniel A. Snyder、Klavs F. Jensen、Peter H. Seeberger

  DOI：10.1039/b414503h

  日期：——

  Glycosylation reactions are performed rapidly over a wide range of conditions as an example of microreactor-based method optimization and process development in organic chemistry.

  作为有机化学中基于微反应器的方法优化和工艺开发的一个实例，糖基化反应可在多种条件下快速进行。
• Catalytic Orthogonal Glycosylation Enabled by Enynal‐Derived Copper Carbenes
  作者：Surya Pratap Singh、Bidhan Ghosh、Indrajeet Sharma

  DOI：10.1002/adsc.202301207

  日期：2024.4.23

  earth-abundant copper carbenes. This method operates under mild conditions and employs readily accessible starting materials, including benchtop stable enynal-derived glycosyl donors, synthesized at the gram scale. The reaction accommodates a variety of glycosyl acceptors, including primary, secondary, and tertiary alcohols. The enynal-derived copper carbenes exhibit remarkable reactivity and selectivity

  在此，我们提出了一种利用地球上丰富的铜卡宾进行催化正交糖基化的方法。该方法在温和条件下操作，并采用易于获得的起始材料，包括以克级合成的台式稳定的烯醛衍生糖基供体。该反应适合多种糖基受体，包括伯醇、仲醇和叔醇。烯醛衍生的铜卡宾表现出显着的反应性和选择性，允许与不同的保护基团和立体化学模式形成糖苷键。该方法提供了对 1,2-顺式和 1,2-反式糖苷键的访问。产物的立体选择性与糖基供体的异头构型无关，其也与广泛使用的炔烃和硫代糖苷供体具有正交反应性。三糖的迭代合成进一步证明了这种正交反应性的应用。
• Synthesis of a tetrasaccharide fragment of cobra venom factor oligosaccharide
  作者：Zhong-Jun Li、Hui Li、Meng-Shen Cai

  DOI：10.1016/s0008-6215(99)00107-x

  日期：1999.7

  Synthesis of a tetrasaccharide fragment, alpha-L-Fuc-(1-->3)-beta-D-GlcNAc-(1-->2)-alpha-D-Man-(1-->6)-alpha-D-Man-OMe of the cobra venom factor (CVF) oligosaccharide is described. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and glycosylation of pyrimidin-2-yl 1-thio-α-d-manno- and -α-l-rhamnopyranoside
  作者：Xianglan Ding、Guangbin Yang、Fanzuo Kong

  DOI：10.1016/s0008-6215(98)00164-5

  日期：1998.8

  Pyrimidin-2-yl 2,3,4,6-tetra-O-benzyl-1-thio-alpha-D-mannopyrano side (9), pyrimidin-2-yl 2,3,4-tri-O-benzyl-alpha-L-rhamnopyranoside (10), pyrimidin-2-yl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-alpha-D-mannopyranoside (7), and pyrimidin-2-y1 2-O-acetyl-3,4-di-O-benzyl-1-thio-alpha-L-rhamnopyranoside (8) were prepared almost quantitatively fi om the corresponding protected 1,2-O-methoxyethylidene-beta-D-manno-or-beta-L-rhamnopyranose with 2-mercaptopyrimidine in the presence of mercuric bromide. Coupling reactions of the thioglycosides promoted by silver triflate with suitable glycosyl accepters afforded 1,2-trans linked disaccharides. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.