(2R,3R,4S,5R,6R)-2-Benzyloxy-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol | 35017-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R,3R,4S,5R,6R)-2-Benzyloxy-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol
• 英文别名: (2R,3R,4S,5R,6R)-2-phenylmethoxy-6-(trityloxymethyl)oxane-3,4,5-triol
• CAS: 35017-03-9
• 化学式: C₃₂H₃₂O₆
• 分子量: 512.602
• InChiKey: XQGMUXAOIHBVMC-GGEKVXJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-2-Benzyloxy-6-trityloxymethyl-tetrahydro-pyran-3,4,5-triol 、 N-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoroundecanoyl)-N-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-beta-alanine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(2R,3S,4S,5R,6R)-4,5-bis[3-[4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoyl(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)amino]propanoyloxy]-6-phenylmethoxy-2-(trityloxymethyl)oxan-3-yl] 3-[4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecanoyl(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)amino]propanoate
  参考文献：
  名称：

  Rapid Oligosaccharide Synthesis Using a Fluorous Protective Group

  摘要：

  The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction and monitored by TLC, NMR, and MS.

  DOI：

  10.1021/jo049425k