methyl 2,3,4-tri-O-benzyl-6-O-(trifluoromethanesulfonyl)-α-D-mannopyranoside | 221545-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-(trifluoromethanesulfonyl)-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl trifluoromethanesulfonate
• CAS: 221545-35-3
• 化学式: C₂₉H₃₁F₃O₈S
• 分子量: 596.622
• InChiKey: BUGPHOJHZLMJFS-MASCHLQQSA-N

物化性质

• 沸点：
  624.1±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(trifluoromethanesulfonyl)-α-D-mannopyranoside 在 palladium dihydroxide 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 6.5h， 生成 methyl 6-deoxy-6-dicarboxymethyl-α-D-mannopyranoside bis(ammonium) salt
  参考文献：
  名称：

  Mono- and Bivalent Ligands Bearing Mannose 6-Phosphate (M6P) Surrogates:  Targeting the M6P/Insulin-Like Growth Factor II Receptor

  摘要：

  Mannose 6-phosphate mimics locked into the alpha-configuration and bearing hydrolase-resistant phosphate surrogates were synthesized and evaluated for binding affinity to the mannose 6-phosphate/insulin-like-growth factor II receptor (M6P/IGF2R). Affinity increases as the phosphate surrogate is varied in the order malonyl ether < malonate < phosphonate. An alkene cross-metathesis approach to sought-after bivalent M6P-bearing ligands is also described. These compounds were designed to map onto biantennary sectors of high-mannose-type oligosaccharides carried by glycoprotein M6P/IGF2R ligands.

  DOI：

  10.1021/ol0479444
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(tertbutyldiphenylsilyl)-α-D-mannopyranoside 在 2,6-二甲基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(trifluoromethanesulfonyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man and the Disaccharides α-d-Man-(1→3)-d-Man and α-d-Man-(1→6)-d-Man

  摘要：

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.

  DOI：

  10.1021/jo020339z

文献信息

• Synthesis of 6,6′-ether linked disaccharides from<scp>d</scp>-allose,<scp>d</scp>-galactose,<scp>d</scp>-glucose and<scp>d</scp>-mannose; evidence on the structure of coyolosa
  作者：Alan H. Haines

  DOI：10.1039/b407468h

  日期：——

  6'-Linked ethers derived from D-allose, D-galactose, D-glucose, and D-mannose have been prepared in order to allow comparisons with the reported 6,6'-linked hexopyranose coyolosa, an hypoglycemic compound which has been isolated by extraction of the root of the palm Acrocomia mexicana. Comparison of NMR data from the ethers and their derived peracetates with corresponding reported data from coyolosa and its

  为了与已报道的6,6'-连接的六吡喃葡萄糖椰油酸酯进行比较，已制备了衍生自D-阿洛糖，D-半乳糖，D-葡萄糖和D-甘露糖的6,6'-连接醚，后者通过提取棕榈Acrocomia mexicana的根来分离。来自醚及其衍生的过乙酸盐的NMR数据与来自油桐及其过乙酸盐的相应报道数据的比较表明，油桐不是6,6'-连接的二糖。合成的化合物代表了一类新型的二糖衍生物，与更常见的头对尾（例如麦芽糖）或头对头（例如海藻糖）二糖相反，它们的尾对尾连接。
• Syntheses of methyl glycosides of 6-deoxyheptoses
  作者：Gerald O. Aspinall、Armando G. McDonald、Ramesh K. Sood

  DOI：10.1139/v94-037

  日期：1994.1.1

  by reduction of the resulting heptopyranosidurononitriles with diisobutylaluminum hydride, hydrolysis of the imine, further reduction with sodium borohydride, and catalytic O-debenzylation, give the corresponding methyl 6-deoxyheptopyranosides. Configurational change at C-4 of methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside to give the talo isomer was effected by oxidation followed

  已经制备了 6-脱氧-D-altro-heptose、6-deoxy-D-manno-heptose 和 6-deoxy-D-talo-heptose 的甲基 α-D-glycopyranosides。用氰化钾置换 2,3,4-三-O-苄基己基己基吡喃糖苷 6-三氟甲磺酸甲酯，然后用二异丁基氢化铝还原生成的吡喃基吡喃糖醛腈，水解亚胺，用硼氢化钠进一步还原，并催化 O-脱苄基，得到相应的甲基 6-脱氧庚基吡喃糖苷。甲基 6-脱氧-7-O-叔丁基二苯基甲硅烷基-α-D-甘露-吡喃庚糖苷在 C-4 处的构型变化以得到 talo 异构体是通过氧化和立体选择性还原来实现的。苷的1H核磁共振数据，
• [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。
• Synthesis of C-Oligosaccharides via Ni-Catalyzed Reductive Hydroglycosylation
  作者：Tayyab Gulzar、Yan-Hua Liu、Yu-Nong Xia、Wei Liu、Pengchao Liu、Dapeng Zhu、Peng Xu、Biao Yu

  DOI：10.1021/acs.orglett.4c00289

  日期：2024.3.1

  metabolically stable surrogates of native glycans containing O/N/S-glycosidic linkages and thus have therapeutic potential. Here we report a straightforward approach to the synthesis of vinyl C-linked oligosaccharides via the Ni-catalyzed reductive hydroglycosylation of alkynyl glycosides with glycosyl bromides.

  C-寡糖是含有O / N / S-糖苷键的天然聚糖的代谢稳定替代物，因此具有治疗潜力。在这里，我们报告了一种通过镍催化炔基糖苷与糖基溴的还原氢糖基化合成乙烯基C-连接寡糖的直接方法。
• [EN] CELL SURFACE RECEPTOR BINDING COMPOUNDS AND CONJUGATES<br/>[FR] COMPOSÉS ET CONJUGUÉS DE LIAISON AU RÉCEPTEUR DE SURFACE CELLULAIRE
  申请人：LYCIA THERAPEUTICS INC

  公开号：WO2021142377A3

  公开（公告）日：2021-10-21