methyl 2-O-benzoyl-α-D-fucopyranoside | 1327154-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-benzoyl-α-D-fucopyranoside
• 英文别名: methyl 3-O-benzoyl-α-D-fucopyranoside；[(2S,3R,4S,5S,6R)-3,5-dihydroxy-2-methoxy-6-methyloxan-4-yl] benzoate
• CAS: 1327154-69-7
• 化学式: C₁₄H₁₈O₆
• 分子量: 282.293
• InChiKey: JGOBTMHDOIPXCR-GQIGJGOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 alpha-d-吡喃半乳糖苷甲酯 在 2,4,6-三甲基吡啶 、 bis(acetylacetonato)dioxidomolybdenum(VI) 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 以85%的产率得到methyl 2-O-benzoyl-α-D-fucopyranoside
  参考文献：
  名称：

  Regioselective Benzoylation of Glycopyranosides by Benzoyl Chloride in the Presence of MoO₂(acac)₂

  摘要：

  Benzoylation of methyl and benzyl glycopyranosides by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst resulted in 3-benzoates with good yield and high regioselectivity. Simple synthesis of the monobenzoates of some glycopyranosides is suggested.

  DOI：

  10.1080/07328303.2010.549258

文献信息

• Regioselective benzoylation of glycopyranosides by benzoic anhydride in the presence of Cu(CF3COO)2
  作者：Evgeny V. Evtushenko

  DOI：10.1016/j.carres.2012.06.020

  日期：2012.10

  Benzoylation of methyl and benzyl glycopyranosides by benzoic anhydride in acetonitrile in the presence of copper(II) trifluoroacetate as a promoter has given monobenzoates with a good yield and high regioselectivity. The composition of monobenzoates depended both on a configuration of hydroxyl groups and on a configuration of aglycone. The simple syntheses of the monobenzoates of some glycosides are

  在三氟乙酸铜（II）作为促进剂的存在下，在乙腈中通过苯甲酸酐在苯甲腈中对甲基和苄基吡喃葡萄糖苷进行苯甲酰化，得到了单苯甲酸酯，具有良好的收率和较高的区域选择性。单苯甲酸酯的组成取决于羟基的构型和糖苷配基的构型。提供了一些糖苷的单苯甲酸酯的简单合成。
• Regioselective Benzoylation of Glycopyranosides by Benzoyl Chloride in the Presence of MoO₂(acac)₂
  作者：E. V. Evtushenko

  DOI：10.1080/07328303.2010.549258

  日期：2010.11.1

  Benzoylation of methyl and benzyl glycopyranosides by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst resulted in 3-benzoates with good yield and high regioselectivity. Simple synthesis of the monobenzoates of some glycopyranosides is suggested.