methyl 2,3-O-isopropylidene-5-deoxy-5-thiocyanato-β-D-ribofuranoside | 158420-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-isopropylidene-5-deoxy-5-thiocyanato-β-D-ribofuranoside
• 英文别名: methyl 5-deoxy-2,3-O-isopropylidene-5-thiocyanato-β-D-ribofuranoside；[(3aR,4R,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl thiocyanate
• CAS: 158420-07-6
• 化学式: C₁₀H₁₅NO₄S
• 分子量: 245.299
• InChiKey: GDWGAWUMBAEQRK-FNCVBFRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  86
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-isopropylidene-5-deoxy-5-thiocyanato-β-D-ribofuranoside 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以95%的产率得到methyl 2,3-O-isopropylidene-5-thio-β-D-ribofuranoside
  参考文献：
  名称：

  糖硫氰酸盐与格氏试剂的反应。硫糖苷的新合成。

  摘要：

  在-40℃下，具有被乙酰基或苯甲酰基保护的羟基的糖基硫氰酸氰酸酯易于与格氏试剂反应，以高收率得到相应的烷基或芳基硫代糖苷。在相似条件下形成在其他位置具有SCN基团的单糖衍生物可形成硫醚。轴向硫氰酸盐不反应。升高的温度引起副反应，导致硫醇。

  DOI：

  10.1016/s0040-4020(01)87009-5
• 作为产物：
  描述：

  potassium thioacyanate 、 1-甲氧基-2,3-O-异亚丙基-5-O-对甲苯磺酰基-beta-D-呋喃核糖苷 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以91%的产率得到methyl 2,3-O-isopropylidene-5-deoxy-5-thiocyanato-β-D-ribofuranoside
  参考文献：
  名称：

  糖硫氰酸盐与格氏试剂的反应。硫糖苷的新合成。

  摘要：

  在-40℃下，具有被乙酰基或苯甲酰基保护的羟基的糖基硫氰酸氰酸酯易于与格氏试剂反应，以高收率得到相应的烷基或芳基硫代糖苷。在相似条件下形成在其他位置具有SCN基团的单糖衍生物可形成硫醚。轴向硫氰酸盐不反应。升高的温度引起副反应，导致硫醇。

  DOI：

  10.1016/s0040-4020(01)87009-5

文献信息

• An unprecedented access to trifluoromethylthiosugar derivatives from thiocyanate precursors upon treatment with trifluoromethyltrimethylsilane
  作者：Marie-Noëlle Bouchu、Sylvie Large、Michaela Steng、Bernard Langlois、Jean-Pierre Praly

  DOI：10.1016/s0008-6215(98)00289-4

  日期：1998.12

  Upon treatment with trifluoromethyltrimethylsilane (2 equiv) in oxolane at 0 degrees C in the presence of a catalytic amount of tetra-n-butylammonium fluoride (0.2 equiv), various protected sugar derivatives having a thiocyanato group attached to different positions (anomeric, secondary, primary) were converted into the corresponding trifluoromethylthio derivatives. Under these conditions, highly selective, albeit partial transformations of primary and secondary thiocyanate groups were achieved while a decreased selectivity was observed when the reaction involved a more reactive anomeric thiocyanate group. However, in this case, lowering the reaction temperature led to enhanced selectivity and higher isolated yields. The isopropylidene and benzoyl protecting groups in the resulting trifluoromethylthiosugar derivatives were removed by standard methods to afford the corresponding free trifluoromethylthio derivatives, generally in high yield and as crystalline solids. Hence, this method opens a practical access to new trifluoromethylthiosugars obtained under smooth conditions as protected or unprotected derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.