2-(5-Deoxy-1,2-O-isopropylidene-α-D-xylo-furanose-5-ylidene)-1,3-dithiane | 155788-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-Deoxy-1,2-O-isopropylidene-α-D-xylo-furanose-5-ylidene)-1,3-dithiane
• 英文别名: (3aR,5R,6S,6aR)-5-(1,3-dithian-2-ylidenemethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 155788-33-3
• 化学式: C₁₂H₁₈O₄S₂
• 分子量: 290.405
• InChiKey: UNWDDMTTZBMORM-APHKKCJPSA-N

物化性质

• 沸点：
  463.5±45.0 °C(predicted)
• 密度：
  1.381±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-Deoxy-1,2-O-isopropylidene-α-D-xylo-furanose-5-ylidene)-1,3-dithiane 在 sodium dithionite 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3aR,5R,6S,6aR)-5-(1-[1,3]Dithian-2-ylidene-2,2,3,3,4,4,5,5,5-nonafluoro-pentyl)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Fluorinated ketene dithioacetals

  摘要：

  Alpha-perfluoroalkyl ketene dithioacetals were synthesized by radical perfluoroalkylation of ketene dithioacetals with perfluoroalkyl iodide and sodium dithionite in a basic medium. Application to sugar derived ketene dithioacetals gave results depending strongly on the sugar structure.

  DOI：

  10.1016/s0040-4039(00)73028-0
• 作为产物：
  描述：

  2-lithio-2-trimethylsilyl-1,3-dithiane 、 1,2-O-异亚丙基-alpha-D-木糖基-戊二醛-1,4-呋喃糖 以 四氢呋喃 为溶剂， 生成 2-(5-Deoxy-1,2-O-isopropylidene-α-D-xylo-furanose-5-ylidene)-1,3-dithiane
  参考文献：
  名称：

  Fluorinated ketene dithioacetals

  摘要：

  Alpha-perfluoroalkyl ketene dithioacetals were synthesized by radical perfluoroalkylation of ketene dithioacetals with perfluoroalkyl iodide and sodium dithionite in a basic medium. Application to sugar derived ketene dithioacetals gave results depending strongly on the sugar structure.

  DOI：

  10.1016/s0040-4039(00)73028-0

文献信息

• Tandem radical trifluoromethylation—nucleophilic cyclization of a glucose-derived ketene dithioacetal. Synthesis of 5-deoxy-5-C-trifluoromethyl-aldurono-6,3-lactones
  作者：Gaëlle Foulard、Thierry Brigaud、Charles Portella

  DOI：10.1016/s0022-1139(98)00223-1

  日期：1998.9

  5-C-trifluoromethylated analogs of d-glucuronolactone and l-iduronolactone was synthesized in a five-step procedure from 1,2-O-isopropylidene-α-d-glucofuranose. The key step involves a tandem radical trifluoromethylation—nucleophilic cyclization of a ketene dithioacetal derived from 1,2-O-isopropylidene-α-d-xylo-pentodialdo-1,4-furanose.

  d-葡糖醛酸内酯的5- C-三氟甲基化类似物和l-异丁烯酸内酯的非对映异构体混合物是由1,2 - O-异亚丙基-α-d-呋喃葡萄糖经五步合成的。关键步骤涉及串联自由基三氟甲基化-衍生自1,2- O-异亚丙基-α-d-二甲苯基-戊二醛-1,4-呋喃糖的乙烯酮二硫缩醛的亲核环化。