2,3,4,6-tetra-O-benzyl-1,5-di-O-tosyl-D-glucitol | 150492-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzyl-1,5-di-O-tosyl-D-glucitol
• 英文别名: [(2S,3R,4S,5R)-5-(4-methylphenyl)sulfonyloxy-2,3,4,6-tetrakis(phenylmethoxy)hexyl] 4-methylbenzenesulfonate
• CAS: 150492-31-2
• 化学式: C₄₈H₅₀O₁₀S₂
• 分子量: 851.051
• InChiKey: WVEXLQONDYMILM-AVNIMNHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  60
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-1,5-di-O-tosyl-D-glucitol 生成 2,3,6-tri-O-benzyl-5-O-toluene-p-sulphonyl-1,4-anhydro-D-glucitol
  参考文献：
  名称：

  C-核苷研究。第13部分。涉及苄氧基参与的2,3,5-三-O-苄基-α（和β）-D-呋喃呋喃糖基乙炔的新合成以及α-Showdomycin的合成

  摘要：

  2,3,4,6-四- ö苄基d -glucitol（5）反应以甲苯p -磺酰基氯在吡啶中于60℃，以形成主要是呋喃产物2,3,6-三ö -苄基-1,4-脱水-D-葡萄糖醇（10）及其5-甲苯-对磺酸酯（11），但失去4- O-苄基。该吡喃产物四ö苄基1,5-脱水- d -glucitol preponderates当中间2,3,4,6-四ö -toluene- p -sulphonyl- d -glucitol（6）转化成其0–5氧阴离子。在新合成的2,3,5-tri- O中已经利用了苄氧基的参与苄基α（及β） - d -ribofuranosylethyne，（20）和（4），从2,3,4,5-四ö苄基醛基- d -核糖。描述了由（20）合成2-α- D-呋喃呋喃糖基马来酰亚胺（Showdomycin的α-异构体）。

  DOI：

  10.1039/p19810002267
• 作为产物：
  描述：

  2,3,4,6-四-O-苄基-D-山梨糖醇 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 48.0h， 以73%的产率得到2,3,4,6-tetra-O-benzyl-1,5-di-O-tosyl-D-glucitol
  参考文献：
  名称：

  Displacement reactions on 2,3,4,6-tetra-O-benzyl-1,5-di-O-sulfonyl-D-glucitols. Synthesis of (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran

  摘要：

  Treatment of the 1,5-dimesylate and 1,5-ditosylate of 2,3,4,6-tetra-O-benzyl-D-glucitol 1 with tetrabutylammonium acetate in acetonitrile leads, through nucleophilic attack by O-2 at C-5 and normal displacement at C-1, to 1-O-acetyl-2,5-anhydro-3,4,6-tri-O-benzyl-L-iditol. In contrast, the corresponding 1,5-ditriflate on similar treatment undergoes displacement at C-1 by attack of O-4 and elimination of triflic acid between C-4 and C-5 to afford (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran.

  DOI：

  10.1039/p19930001003

文献信息

• C-nucleoside studies. Part 13. A new synthesis of 2,3,5-tri-O-benzyl-α(and β)-<scp>D</scp>-ribofuranosylethyne involving benzyloxy participation, and a synthesis of α-showdomycin
  作者：Gaffar Aslani-Shotorbani、J. Grant Buchanan、Alan R. Edgar、Colin T. Shanks、Gavin C. Williams

  DOI：10.1039/p19810002267

  日期：——

  when the intermediate 2,3,4,6-tetra-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its 0–5 oxyanion. Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-α(and β)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose. A synthesis of 2-α-D-ribofuranosylmaleimide, the α-isomer of showdomycin, from (20) is described.

  2,3,4,6-四- ö苄基d -glucitol（5）反应以甲苯p -磺酰基氯在吡啶中于60℃，以形成主要是呋喃产物2,3,6-三ö -苄基-1,4-脱水-D-葡萄糖醇（10）及其5-甲苯-对磺酸酯（11），但失去4- O-苄基。该吡喃产物四ö苄基1,5-脱水- d -glucitol preponderates当中间2,3,4,6-四ö -toluene- p -sulphonyl- d -glucitol（6）转化成其0–5氧阴离子。在新合成的2,3,5-tri- O中已经利用了苄氧基的参与苄基α（及β） - d -ribofuranosylethyne，（20）和（4），从2,3,4,5-四ö苄基醛基- d -核糖。描述了由（20）合成2-α- D-呋喃呋喃糖基马来酰亚胺（Showdomycin的α-异构体）。
• Displacement reactions on 2,3,4,6-tetra-O-benzyl-1,5-di-O-sulfonyl-D-glucitols. Synthesis of (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran
  作者：Paul A. Fowler、Alan H. Haines、Richard J. K. Taylor、Ewan J. T. Chrystal、Michael B. Gravestock

  DOI：10.1039/p19930001003

  日期：——

  Treatment of the 1,5-dimesylate and 1,5-ditosylate of 2,3,4,6-tetra-O-benzyl-D-glucitol 1 with tetrabutylammonium acetate in acetonitrile leads, through nucleophilic attack by O-2 at C-5 and normal displacement at C-1, to 1-O-acetyl-2,5-anhydro-3,4,6-tri-O-benzyl-L-iditol. In contrast, the corresponding 1,5-ditriflate on similar treatment undergoes displacement at C-1 by attack of O-4 and elimination of triflic acid between C-4 and C-5 to afford (3R,4S)-3,4-dibenzyloxy-2-(2-benzyloxyethylidene)tetrahydrofuran.