(2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(4-methoxy-phenyl)-tetrahydro-pyran-3,4,5-triol | 117772-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(4-methoxy-phenyl)-tetrahydro-pyran-3,4,5-triol
• CAS: 117772-56-2
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: VVFBMGVHEBHTRM-UJPOAAIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(4-methoxy-phenyl)-tetrahydro-pyran-3,4,5-triol 、 alkaline earth salt of/the/ methylsulfuric acid 生成 1-methoxy-4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)benzene
  参考文献：
  名称：

  Stereodirected Synthesis of Aryl α-C-Glycosides from 2-O-Arylsilyl-glucopyranosides

  摘要：

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.

  DOI：

  10.1021/ol035529q
• 作为产物：
  描述：

  (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-tetrahydro-pyran-3-ol 在 钯 氢气 作用下， 生成 (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(4-methoxy-phenyl)-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Stereodirected Synthesis of Aryl α-C-Glycosides from 2-O-Arylsilyl-glucopyranosides

  摘要：

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.

  DOI：

  10.1021/ol035529q