6-deoxy-β-D-altropyranose | 73-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-β-D-altropyranose
• 英文别名: D-6-deoxy-altrose；β-D-6-deoxy-altropyranose；6-Desoxy-D-altrose；(2R,3S,4R,5S,6R)-6-methyloxane-2,3,4,5-tetrol
• CAS: 73-34-7；87-96-7；488-79-9；551-63-3；609-01-8；643-17-4；643-18-5；4164-09-4；6014-42-2；6155-36-8；6189-71-5；6696-41-9；6736-43-2；13224-93-6；22611-09-2；28161-49-1；28161-50-4；28161-52-6；45864-36-6；63814-64-2；71116-59-1；71116-61-5；72598-05-1；87936-88-7；87936-89-8；97466-79-0；116908-82-8；120442-60-6；123484-22-0；133576-32-6
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: SHZGCJCMOBCMKK-DGPNFKTASA-N

物化性质

• 熔点：
  144.5-145 °C
• 沸点：
  323.9±42.0 °C(Predicted)
• 密度：
  1.556±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-methoxyphenyl 3-O-benzyl-α-D-rhamnopyranoside 在 吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 ammonium cerium (IV) nitrate 、 20% palladium(II) hydroxide on carbon 、 水 、 氢气 、 sodium methylate 、 4-甲基苯磺酸吡啶 作用下， 以 1,4-二氧六环 、 吡啶 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 85.0 ℃ 、101.33 kPa 条件下， 反应 14.5h， 生成 6-deoxy-β-D-altropyranose 、 6-deoxy-α-D-altrose
  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

• 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
  作者：Hideharu Ishida、Masashi Yamada、Fumi Yoshida、Hiromune Ando、Makoto Kiso、Masakuni Tako

  DOI：10.3987/com-10-s(e)107

  日期：——

  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.