(2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((2R,3R,4S,5R)-3,4,5-tris(benzoyloxy)-6-bromotetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate | 855662-13-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((2R,3R,4S,5R)-3,4,5-tris(benzoyloxy)-6-bromotetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
• CAS: 855662-13-4
• 化学式: C₆₁H₄₉BrO₁₇
• 分子量: 1133.95
• InChiKey: SBABKVJCLJOXND-QCOQHBDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  79.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  12-羟基硬脂酸甲酯 、 (2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((2R,3R,4S,5R)-3,4,5-tris(benzoyloxy)-6-bromotetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate 在 silver perchlorate 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis of 12-O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

  摘要：

  Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and Koening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated T cells (NFAT)-green fluorescent protein (GFP) revealed that four dimannopyranosyl-oxystearate analogues were Mincle agonists and that 12-O-(2-O-alpha-D-mannopyranosyl)-alpha-D-mannopyranosyl-oxystearate was as an activator of both mouse and human Mincle.

  DOI：

  10.1021/acsmedchemlett.8b00413
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->6)-1,2,3,4-tetra-O-benzoyl-D-glucopyranoside 在 氢溴酸 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R,3R,4S,5R,6R)-2-((benzoyloxy)methyl)-6-(((2R,3R,4S,5R)-3,4,5-tris(benzoyloxy)-6-bromotetrahydro-2H-pyran-2-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  Synthesis of 12-O-Mono- and Diglycosyl-oxystearates, a New Class of Agonists for the C-type Lectin Receptor Mincle

  摘要：

  Fifteen glycosyl-oxystearates were synthesized by Crich's 4,6-benzylidene and Koening-Knorr strategies. Assessment of structure-activity relationships using macrophage-inducible C-type lectin (Mincle) receptor cells expressing nuclear factor of activated T cells (NFAT)-green fluorescent protein (GFP) revealed that four dimannopyranosyl-oxystearate analogues were Mincle agonists and that 12-O-(2-O-alpha-D-mannopyranosyl)-alpha-D-mannopyranosyl-oxystearate was as an activator of both mouse and human Mincle.

  DOI：

  10.1021/acsmedchemlett.8b00413

文献信息

• Stannylene-Mediated Regioselective 6-<i>O</i>-Glycosylation of Unprotected Phenyl 1-Thioglycopyranosides
  作者：Agnese Maggi、Robert Madsen

  DOI：10.1002/ejoc.201300026

  日期：2013.5

  straightforward procedure is described for the synthesis of (16)-linked saccharides by regioselective glycosylation of unprotected glycosyl acceptors. Phenyl 1-thioglycopyranosides derived from D-glucose, D-galactose and D-mannose were treated with dibutyltin oxide to introduce a stannylene acetal, and then subjected to selective glycosylation at the 6-position with the Koenigs–Knorr protocol. Peracylated glycosyl

  描述了通过未受保护的糖基受体的区域选择性糖基化合成 (16) 连接的糖类的简单程序。衍生自 D-葡萄糖、D-半乳糖和 D-甘露糖的苯基 1-巯基吡喃糖苷用氧化二丁基锡处理以引入亚锡基缩醛，然后使用 Koenigs-Knorr 方案在 6 位进行选择性糖基化。D-葡萄糖、D-半乳糖、D-甘露糖和D-葡糖胺的过酰化糖基溴化物用作供体，以中等至良好的产率得到相应的(16)-连接的二糖。使用衍生自 D-葡萄糖和 D-半乳糖的糖基供体和受体获得最佳结果。完全酰化的二糖硫糖苷也可以作为区域选择性偶联的糖基供体。