(2R,4R,5S,6R)-5-[(4-methoxyphenyl)methoxy]-6-methyloxane-2,4-diol | 1561049-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4R,5S,6R)-5-[(4-methoxyphenyl)methoxy]-6-methyloxane-2,4-diol
• CAS: 1561049-41-9
• 化学式: C₁₄H₂₀O₅
• 分子量: 268.31
• InChiKey: UZXHJGWHUMPEBM-ICGCDAGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2R,3S,4R)-2-Methyl-3,4-dihydro-2H-pyran-3,4-diol 在 咪唑 、 N-溴代丁二酰亚胺(NBS) 、 ReOCl₃(SMe₂)(OPPh₃) 、 四丁基氟化铵 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 42.25h， 生成 、 (2R,4R,5S,6R)-5-[(4-methoxyphenyl)methoxy]-6-methyloxane-2,4-diol
  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

• Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric <i>O</i>-Alkylation with Secondary Electrophiles
  作者：Danyang Zhu、Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/ja4116956

  日期：2014.2.26

  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.