| 1561048-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1561048-53-0
• 化学式: C₂₇H₂₇F₃O₆S₂
• 分子量: 568.635
• InChiKey: QHQBNOHPQLNOBM-WBPROUHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  、 在 sodium hydride 、 15-冠醚-5 作用下， 以 1,4-二氧六环 、 mineral oil 为溶剂， 反应 24.17h， 以88%的产率得到
  参考文献：
  名称：

  Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric O-Alkylation with Secondary Electrophiles

  摘要：

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.

  DOI：

  10.1021/ja4116956
• 作为产物：
  描述：

  phenyl 2-O-benzyl-6-deoxy-1-thio-β-D-allopyranoside 在 吡啶 、 二苯基酸 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.0h， 生成
  参考文献：
  名称：

  Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric O-Alkylation with Secondary Electrophiles

  摘要：

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.

  DOI：

  10.1021/ja4116956

文献信息

• Stereoselective Construction of β‐Mannopyranosides by Anomeric <i>O</i> ‐Alkylation: Synthesis of the Trisaccharide Core of <i>N</i> ‐linked Glycans
  作者：Hai Nguyen、Danyang Zhu、Xiaohua Li、Jianglong Zhu

  DOI：10.1002/anie.201600488

  日期：2016.4.4

  for direct and stereoselective synthesis of β‐mannopyranosides by anomeric O‐alkylation has been developed. This anomeric O‐alkylation of mannopyranose‐derived lactols is proposed to occur under synergistic control of a kinetic anomeric effect and metal chelation. The presence of a conformationally flexible C6 oxygen atom in the sugar‐derived lactol donors is required for this anomeric O‐alkylation to

  开发了一种通过异头O-烷基化直接和立体选择性合成β-甘露聚糖的新方法。甘露聚糖吡喃糖衍生的乳糖醇的这种异头O-烷基化被提议在动力学异头作用和金属螯合的协同控制下发生。为了使这种端基异构O-烷基化有效，需要糖衍生的乳糖醇供体中存在构象柔性的C6氧原子，这可能是由于其与铯离子的螯合。相反，C 2氧原子的存在起着较小的作用。这种糖基化方法已成功用于合成复杂的N-连接聚糖的三糖核心。
• Stereoselective Synthesis of α-Digitoxosides and α-Boivinosides via Chelation-Controlled Anomeric<i>O</i>-Alkylation
  作者：Danyang Zhu、Surya Adhikari、Kedar N. Baryal、Belal N. Abdullah、Jianglong Zhu

  DOI：10.1080/07328303.2014.931965

  日期：2014.10.13

  A chelation-controlled anomeric O-alkylation has been developed for the stereoselective synthesis of α-digitoxosides and α-boivinosides bearing a C3-free hydroxyl group. Due to chelation via sodium ion, the anomeric alkoxides are locked in the axial configuration, which leads to the selective production of α-glycosides.

  已经开发了螯合控制的异头O-烷基化反应，用于立体选择性地合成α-数字氧苷和带有C3-游离羟基的α-boivinosides。由于经由钠离子的螯合，异头醇盐被锁定在轴向构型中，这导致选择性产生α-糖苷。