methyl 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-gluco-octonate | 161721-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-gluco-octonate
• 英文别名: methyl (4S)-4-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxybutanoate
• CAS: 161721-27-3
• 化学式: C₁₅H₂₆O₇
• 分子量: 318.367
• InChiKey: HCPODNDODZHKPZ-XKAARJIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-gluco-octonate 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以87%的产率得到2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-gluco-octono-1,4-lactone
  参考文献：
  名称：

  A synthesis of 3-deoxy-D-gluco-oct-2-ulosonic acid

  摘要：

  Acyclic 2:3,5:6- and 3:4,5:6-di-O-isopropylidene-D-glucoses have been converted by four reactions involving a Wittig chain homologation, a catalytic hydrogenation, an acid hydrolysis and an acetonation into 2,3-dideoxy-5:6,7:8-di-O-isopropylidene-D-gluco-octono-1,4-lactone which underwent a Wasserman reaction and then a hydrolysis to yield 3-deoxy-D-gluco-oct-2-ulosonic acid, isolated as its ammonium salt 2.

  DOI：

  10.1016/s0957-4166(00)80388-2
• 作为产物：
  描述：

  3,4:5,6-di-O-isopropylidene-D-glucose diethyl dithioacetal 在 palladium on activated charcoal 氢气 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 水 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.08h， 生成 methyl 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-gluco-octonate
  参考文献：
  名称：

  A synthesis of 3-deoxy-D-gluco-oct-2-ulosonic acid

  摘要：

  Acyclic 2:3,5:6- and 3:4,5:6-di-O-isopropylidene-D-glucoses have been converted by four reactions involving a Wittig chain homologation, a catalytic hydrogenation, an acid hydrolysis and an acetonation into 2,3-dideoxy-5:6,7:8-di-O-isopropylidene-D-gluco-octono-1,4-lactone which underwent a Wasserman reaction and then a hydrolysis to yield 3-deoxy-D-gluco-oct-2-ulosonic acid, isolated as its ammonium salt 2.

  DOI：

  10.1016/s0957-4166(00)80388-2

文献信息

• A synthesis of 3-deoxy-D-gluco-oct-2-ulosonic acid
  作者：Tony K.M. Shing

  DOI：10.1016/s0957-4166(00)80388-2

  日期：1994.12

  Acyclic 2:3,5:6- and 3:4,5:6-di-O-isopropylidene-D-glucoses have been converted by four reactions involving a Wittig chain homologation, a catalytic hydrogenation, an acid hydrolysis and an acetonation into 2,3-dideoxy-5:6,7:8-di-O-isopropylidene-D-gluco-octono-1,4-lactone which underwent a Wasserman reaction and then a hydrolysis to yield 3-deoxy-D-gluco-oct-2-ulosonic acid, isolated as its ammonium salt 2.