4-methoxyphenyl 2,4-di-O-acetyl-α-D-rhamnopyranoside | 1304123-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 2,4-di-O-acetyl-α-D-rhamnopyranoside
• CAS: 1304123-39-4
• 化学式: C₁₇H₂₂O₈
• 分子量: 354.357
• InChiKey: XZTCZLNFBAAPKD-PETBAYLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 2,4-di-O-acetyl-α-D-rhamnopyranoside 在 吡啶 、 甲醇 、 ammonium cerium (IV) nitrate 、 sodium methylate 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 11.5h， 生成
  参考文献：
  名称：

  Synthesis of 6-Deoxy-D-altrose Used as an Authentic Sample to Identify an Unknown Monosaccharide Isolated from the Fruiting Body of an Edible Mushroom

  摘要：

  Here, we describe the synthesis of 6-deoxy-D-altrose and its subsequent use as an authentic sample to verify the structure of a monosaccharide newly isolated from the fruiting body of an edible mushroom. D-Rhamnopyranoside, converted from D-mannopyranoside, was selectively protected to give the 3-OH derivative, which was converted to the corresponding 6-deoxy-D-altropyranoside by nucleophilic substitution of the 3-triflate with acetoxy group. Removal of the protecting group, including the temporary protection of the anomeric position with the THP group, afforded the desired 6-deoxy-D-altrose. Both the NMR data and the [alpha](D) value were identical to the data on the natural product, thus indicating that the recently isolated monosaccharide was 6-deoxy-D-altrose.

  DOI：

  10.3987/com-10-s(e)107
• 作为产物：
  描述：

  p-methoxyphenyl α-D-rhamnopyranoside 在 4-二甲氨基吡啶 、 20% palladium(II) hydroxide on carbon 、 氢气 、 二正丁基氧化锡 作用下， 以 1,4-二氧六环 、 吡啶 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 4-methoxyphenyl 2,4-di-O-acetyl-α-D-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of 6-Deoxy-D-altrose Used as an Authentic Sample to Identify an Unknown Monosaccharide Isolated from the Fruiting Body of an Edible Mushroom

  摘要：

  Here, we describe the synthesis of 6-deoxy-D-altrose and its subsequent use as an authentic sample to verify the structure of a monosaccharide newly isolated from the fruiting body of an edible mushroom. D-Rhamnopyranoside, converted from D-mannopyranoside, was selectively protected to give the 3-OH derivative, which was converted to the corresponding 6-deoxy-D-altropyranoside by nucleophilic substitution of the 3-triflate with acetoxy group. Removal of the protecting group, including the temporary protection of the anomeric position with the THP group, afforded the desired 6-deoxy-D-altrose. Both the NMR data and the [alpha](D) value were identical to the data on the natural product, thus indicating that the recently isolated monosaccharide was 6-deoxy-D-altrose.

  DOI：

  10.3987/com-10-s(e)107

文献信息

• Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides
  作者：Jianbo Zhang、Youxian Dong、Madina Yuma、Yuling Mei、Nan Jiang、Guofang Yang、Zhongfu Wang

  DOI：10.1055/s-0040-1707098

  日期：2020.7

  acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

  开发了一种基于 Cu(II) 催化反应合成 2-脱氧-O-半乳糖苷的有效糖基化方法，无需额外配体。糖基化适用于不同的受保护糖基供体和广泛的受体，包括醇、氨基酸、糖和苯酚，并且在温和条件下以优异的收率和高α-选择性进行。该反应在克级规模上很容易进行，其多功能性体现在低聚糖的合成中。