2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-gluco-octono-1,4-lactone | 161721-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dideoxy-5,6:7,8-di-O-isopropylidene-D-gluco-octono-1,4-lactone
• 英文别名: (5S)-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: 161721-24-0
• 化学式: C₁₄H₂₂O₆
• 分子量: 286.325
• InChiKey: UFWZOUTVESKUEV-LUTQBAROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-dideoxy-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 481.33h， 生成 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 ℃ 、101.33 kPa 条件下， 反应 12.08h， 生成 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

文献信息

• New Radical Approaches to 3-Deoxy-<scp>d</scp>-oct-2-ulosonic Acids (KDO)
  作者：Torsten Linker、Boo Geun Kim、Uwe Schilde

  DOI：10.1055/s-2005-865325

  日期：——

  led to key intermediates in the synthesis of 3-deoxy-D-oct-2-ulosonic acids (KDO). Manganese(III) acetate and cerium(IV) ammonium nitrate were the reagents of choice for the oxidative generation of radicals, whereas samarium(II) iodide was employed for reductive couplings. Both strategies were realized by using easily available starting materials, with acetic acid as C 2 and ethyl acrylate as C 3

  两种不同的方法，用不饱和碳水化合物作为自由基受体和碳水化合物衍生的醛作为自由基前体，导致合成 3-脱氧-D-辛-2-超声酸 (KDO) 的关键中间体。乙酸锰 (III) 和硝酸铈 (IV) 铵是自由基氧化生成的首选试剂，而碘化钐 (II) 用于还原偶联。这两种策略都是通过使用容易获得的起始材料实现的，分别以乙酸作为 C 2 和丙烯酸乙酯作为 C 3 结构单元。