3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol | 912845-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol
• 英文别名: [(2R,3R,4R,5R,6R)-6-ethynyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 912845-21-7
• 化学式: C₂₉H₃₀O₅
• 分子量: 458.554
• InChiKey: GLCVILFMHCRHME-HWVUQVAQSA-N

物化性质

• 沸点：
  589.5±50.0 °C(predicted)
• 密度：
  1.20±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol 在 咪唑 、 碘 、 三苯基膦 作用下， 生成
  参考文献：
  名称：

  Modular Approach to Triazole-Linked 1,6-α-d-Oligomannosides to the Discovery of Inhibitors of Mycobacterium tuberculosis Cell Wall Synthetase

  摘要：

  Aiming at developing inhibitors of mannosyltransferases, the enzymes that participate in the biosynthesis of the cell envelope of Mycobacterium tuberculosis, the synthesis of a range of designed triazole-linked 1,6-oligomannosides up to a hexadecamer has been accomplished by a modular approach centered on the Cu(I)-catalyzed azide-alkyne cycloaddition as key process. The efficiency and fidelity of the cycloaddition are substantiated by high yields (76-96%) and exclusive formation of the expected 1,4-disubstituted triazole ring in all oligomer assembling reactions. Key features of oligomers thus prepared are the anomeric carbon-carbon bond of all mannoside residues and the 6-deoxymannoside capping residue. Suitable bioassays with dimer, tetramer, hexamer, octamer, decamer, and hexadecamer showed variable inhibitor activity against mycobacterial alpha-(1,6)-mannosyltransferases, the highest activity (IC50 = 0.14-0.22 mM) being registered with the hexamannoside and octamannoside.

  DOI：

  10.1021/jo100928g
• 作为产物：
  描述：

  (6-O-acetyl-2,3,4-tri-O-benzyl-α-D-mannopyranosyl)ethyne 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以420 mg的产率得到3,7-anhydro-4,5,6-tri-O-benzyl-1,2-dideoxy-D-glycero-D-talo-oct-1-ynitol
  参考文献：
  名称：

  第一次合成1,2,3-三唑并连接的（1,6）-α-D-低聚甘露糖（三唑甘露糖）是通过Cu（I）催化的炔-叠氮化物环加成反应进行的。

  摘要：

  乙炔基α-C-甘露糖苷和烷基6-叠氮基-α-C-甘露糖苷衍生物之间的铜（I）迭代铜（I）催化的环加成反应适合α-D-之间的（1,6）-连接甘露糖单元通过1,4-二取代的三唑桥，从而形成线性低聚物（产率为80-90％），三唑和甘露糖片段交替排列，直至三唑-五甘露糖衍生物。

  DOI：

  10.1039/b609734k

文献信息

• [EN] M6PR CELL SURFACE RECEPTOR BINDING COMPOUNDS AND CONJUGATES<br/>[FR] COMPOSÉS ET CONJUGUÉS DE LIAISON AU RÉCEPTEUR DE SURFACE CELLULAIRE M6PR
  申请人：LYCIA THERAPEUTICS INC

  公开号：WO2023288015A1

  公开（公告）日：2023-01-19

  The present disclosure provides a class of compounds including a ligand moiety that specifically binds to a cell surface mannose-6-phosphate receptor (M6PR). The M6PR binding compounds can trigger the receptor to internalize into the cell a bound compound. The ligand moieties of this disclosure can be linked to a variety of moieties of interest without impacting the specific binding to, and function of, the M6PR. Also provided are compound that are conjugates of the ligand moieties linked to a biomolecule, such as an antibody, which conjugates can harness cellular pathways to remove specific target proteins from the cell surface or the extracellular milieu. For example, the conjugates described herein may sequester and/or degrade a target molecule of interest in a cell's lysosome. Also provided are methods of using the conjugates to target a protein for sequestration and/or lysosomal degradation.

  本公开提供了一类化合物，包括一个配体基团，该基团专门结合细胞表面的甘露醇-6-磷酸受体（M6PR）。M6PR结合化合物可以触发受体内部化到细胞中结合的化合物。本公开的配体基团可以与各种感兴趣的基团链接，而不会影响对M6PR的特异性结合和功能。还提供了化合物，它们是与生物分子（例如抗体）连接的配体基团的共轭物，这些共轭物可以利用细胞途径从细胞表面或细胞外环境中去除特定的靶蛋白质。例如，本文所述的共轭物可以在细胞溶酶体中固定和/或降解感兴趣的靶分子。还提供了使用共轭物来靶向蛋白质进行固定和/或溶酶体降解的方法。