| 1561048-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1561048-46-1
• 化学式: C₁₆H₂₁F₃O₇S
• 分子量: 414.4
• InChiKey: TXYHKJJIFHVPMV-BSLXNSKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  80.29
• 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72%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：

  (2S,3R,4S)-4-((4-methoxybenzyl)oxy)-2-methyl-3,4-dihydro-2H-pyran-3-ol 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 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 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。