2,3-dideoxy-2-(dimethylaminomethylene)-5,6:7,8-di-O-isopropylidene-D-gluco-octono-1,4-lactone | 161814-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dideoxy-2-(dimethylaminomethylene)-5,6:7,8-di-O-isopropylidene-D-gluco-octono-1,4-lactone
• 英文别名: (3E,5S)-3-(dimethylaminomethylidene)-5-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-2-one
• CAS: 161814-36-4
• 化学式: C₁₇H₂₇NO₆
• 分子量: 341.404
• InChiKey: YSYBNYYJNRFYPE-NXIBAVPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-dideoxy-2-(dimethylaminomethylene)-5,6:7,8-di-O-isopropylidene-D-gluco-octono-1,4-lactone 在 氧气 、 亚甲兰 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 以90%的产率得到3-deoxy-5,6:7,8-di-O-isopropylidene-D-gluco-oct-2-ulosono-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 、 对甲苯磺酸 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 水 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 25.0~70.0 ℃ 、101.33 kPa 条件下， 反应 492.08h， 生成 2,3-dideoxy-2-(dimethylaminomethylene)-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

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.