methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-D-fructofuranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-D-fructofuranoside
• 英文别名: (4aS,6S,7S,7aS)-6-(bromomethyl)-4a-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-7-ol
• 化学式: C₁₀H₁₇BrO₅
• 分子量: 297.146
• InChiKey: VIAQETWPCUIPCW-ODXREFDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-D-fructofuranoside 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以98%的产率得到
  参考文献：
  名称：

  The First Chemical Synthesis of 6-Thio-D-fructopyranose via Methyl 6-Bromo-6-deoxy-1,3-O-isopropylidene-α-D-fructofuranoside as a Key Intermediate

  摘要：

  Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-alpha-D-fructofuranoside (4). The first chemical synthesis of 6-thio-D-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.

  DOI：

  10.3987/com-06-10965
• 作为产物：
  描述：

  2,2-二甲氧基丙烷 、 蔗糖 在 对甲苯磺酸 、 吡啶 、 四溴化碳 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以52%的产率得到methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-D-fructofuranoside
  参考文献：
  名称：

  The First Chemical Synthesis of 6-Thio-D-fructopyranose via Methyl 6-Bromo-6-deoxy-1,3-O-isopropylidene-α-D-fructofuranoside as a Key Intermediate

  摘要：

  Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-alpha-D-fructofuranoside (4). The first chemical synthesis of 6-thio-D-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.

  DOI：

  10.3987/com-06-10965

文献信息

• The First Chemical Synthesis of 6-Thio-D-fructopyranose via Methyl 6-Bromo-6-deoxy-1,3-O-isopropylidene-α-D-fructofuranoside as a Key Intermediate
  作者：Tadashi Hanaya、Nobuaki Sato、Hiroshi Yamamoto

  DOI：10.3987/com-06-10965

  日期：——

  Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-alpha-D-fructofuranoside (4). The first chemical synthesis of 6-thio-D-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.