methyl (S)-2-phenyl-2-{[(2R,4R)-4-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl]oxy}acetate | 1314380-03-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (S)-2-phenyl-2-{[(2R,4R)-4-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl]oxy}acetate
• 英文别名: methyl (2S)-2-phenyl-2-[[(2R,4R)-6-(1,3-thiazol-2-yl)-4-[[(2R,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-3,4-dihydro-2H-pyran-2-yl]oxy]acetate
• CAS: 1314380-03-4
• 化学式: C₅₂H₅₃NO₉S
• 分子量: 868.06
• InChiKey: CLFQYBYIHBVEAH-WZKPMMDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  63
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-phenyl-2-{[(2R,4R)-4-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl]oxy}acetate 在 lithium aluminium tetrahydride 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以6.34 g的产率得到(S)-2-phenyl-2-(((2R,4R)-6-(thiazol-2-yl)-4-(((2R,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)-3,4-dihydro-2H-pyran-2-yl)oxy)ethan-1-ol
  参考文献：
  名称：

  Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

  摘要：

  The corresponding oxadiene, prepared from the starting perbenzylated alpha-D-mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3-C-alpha-D-mannosylated 1,2-D-glucal and 3-C-alpha-D-mannosylated 1,2-L-glucal were prepared. A simple epimerisation of the starting alpha-D-mannopyranosylethanal afforded perbenzylated beta-D-mannopyranosylethanal, which was converted to 3-C-beta-D-mannosylated 1,2-D-glucal or to 3-C-beta-D-mannosylated 1,2-L-glucal by the same procedure. The structure of the obtained 3-C-alpha-D-mannosylated 1,2-D-glucal has been confirmed independently by its transformation to the known peracetylated methyl alpha-C-(1 -> 3)-mannobioside. The prepared glucals are suitable precursors for the synthesis of stable glycoconjugates with non-hydrolyzable mannose-containing epitopes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.044
• 作为产物：
  描述：

  1-(thiazol-2-yl)-2-(triphenyl-λ⁵-phosphanylidene)ethan-1-one 在 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 96.0h， 生成 methyl (S)-2-phenyl-2-{[(2R,4R)-4-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)methyl-6-(thiazol-2-yl)-3,4-dihydro-2H-pyran-2-yl]oxy}acetate
  参考文献：
  名称：

  Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

  摘要：

  The corresponding oxadiene, prepared from the starting perbenzylated alpha-D-mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3-C-alpha-D-mannosylated 1,2-D-glucal and 3-C-alpha-D-mannosylated 1,2-L-glucal were prepared. A simple epimerisation of the starting alpha-D-mannopyranosylethanal afforded perbenzylated beta-D-mannopyranosylethanal, which was converted to 3-C-beta-D-mannosylated 1,2-D-glucal or to 3-C-beta-D-mannosylated 1,2-L-glucal by the same procedure. The structure of the obtained 3-C-alpha-D-mannosylated 1,2-D-glucal has been confirmed independently by its transformation to the known peracetylated methyl alpha-C-(1 -> 3)-mannobioside. The prepared glucals are suitable precursors for the synthesis of stable glycoconjugates with non-hydrolyzable mannose-containing epitopes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.044

文献信息

• Nonhydrolyzable C-disaccharides, a new class of DC-SIGN ligands
  作者：Benedetta Bertolotti、Beáta Oroszová、Ieva Sutkeviciute、Ladislav Kniežo、Franck Fieschi、Kamil Parkan、Zuzana Lovyová、Martina Kašáková、Jitka Moravcová

  DOI：10.1016/j.carres.2016.09.005

  日期：2016.11

  based on d-manno and l-fuco configurations as prospective DC-SIGN ligands. In particular, the l-fucose glycomimetics were more active than the respective d-mannose ones. The highest affinity was assessed for simple 1,4-bis(alpha-l-fucopyranosyl)butane (SPR: IC50 0.43 mM) that displayed about twice higher activity than natural ligand Lex. Our results make C-glycosides attractive candidates for multivalent

  由于这种C型凝集素在感染过程中的重要性，发现DC-SIGN受体有效配体是抗病毒药物设计最具挑战性的概念之一。DC-SIGN识别甘露糖基化和岩藻糖基化的寡糖，但糖苷键可用于化学和酶促降解。为了避免这个问题，稳定的糖苷模拟物的合成已引起越来越多的关注。在这项工作中，我们首次建立了基于d-甘露聚糖和l-fuco构型的单价和二价C-糖苷作为预期的DC-SIGN配体。特别地，l-岩藻糖糖模拟物比相应的d-甘露糖糖模拟物更具活性。对于显示出比天然配体Lex高约两倍的活性的简单1,4-双（α-1-呋喃核糖基）丁烷（SPR：IC50 0.43 mM）评估了最高亲和力。