methyl α-D-2,3,6-tri-O-benzyl-4-vinyl-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-D-2,3,6-tri-O-benzyl-4-vinyl-glucopyranoside
• 英文别名: (2S,3R,4S,5R,6R)-5-ethenoxy-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• 化学式: C₃₀H₃₄O₆
• 分子量: 490.596
• InChiKey: RWPJLWWELQIXDK-RLXMVLCYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷	methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside	19488-48-3	C28H32O6	464.558

反应信息

• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 乙烯基正丁醚 在 air 、 4,7-二苯基-1,10-菲罗啉 、 palladium diacetate 作用下， 以69%的产率得到methyl α-D-2,3,6-tri-O-benzyl-4-vinyl-glucopyranoside
  参考文献：
  名称：

  Palladium(II)-Catalyzed Transfer Vinylation of Protected Monosaccharides

  摘要：

  A method for the catalytic vinylation of protected monosaccharides bearing a single free hydroxyl function has been developed. Reaction of representative primary, secondary, and anomeric sugar hydroxyl functions with butyl vinyl ether as the reactant and solvent and (phen)Pd-(OAc)(2) (phen = 1,10-phenanthroline ligand) as the catalyst gives the corresponding vinylated sugar products in 36-79% yield. The catalyst requires the presence of traces of oxygen in the reaction mixture to prevent decomposition to Pd(0).

  DOI：

  10.1021/ol017104e

文献信息

• Palladium(II)-Catalyzed Transfer Vinylation of Protected Monosaccharides
  作者：Sean Handerson、Marcel Schlaf

  DOI：10.1021/ol017104e

  日期：2002.2.1

  A method for the catalytic vinylation of protected monosaccharides bearing a single free hydroxyl function has been developed. Reaction of representative primary, secondary, and anomeric sugar hydroxyl functions with butyl vinyl ether as the reactant and solvent and (phen)Pd-(OAc)(2) (phen = 1,10-phenanthroline ligand) as the catalyst gives the corresponding vinylated sugar products in 36-79% yield. The catalyst requires the presence of traces of oxygen in the reaction mixture to prevent decomposition to Pd(0).