N'-(β-D-mannopyranosyl)-p-toluenesulfonohydrazide | 1387537-58-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N'-(β-D-mannopyranosyl)-p-toluenesulfonohydrazide
• 英文别名: 4-methyl-N'-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]benzenesulfonohydrazide
• CAS: 1387537-58-7
• 化学式: C₁₃H₂₀N₂O₇S
• 分子量: 348.377
• InChiKey: QFTMHKHHOVFAMI-NAWOPXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N'-(β-D-mannopyranosyl)-p-toluenesulfonohydrazide 在 2-甲基-2-恶唑啉 、 磷酸 、 copper dichloride 、 barium(II) hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 乙醇 、 水 为溶剂， 反应 18.0h， 以45%的产率得到barium α-D-mannopyranosyl-1-phosphate
  参考文献：
  名称：

  Protecting-Group-Free Synthesis of Glycosyl 1–Phosphates

  摘要：

  Glycosyl 1-phosphates enriched in the alpha-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.

  DOI：

  10.1021/ol3019083
• 作为产物：
  描述：

  D-甘露糖 、 对甲苯磺酰肼 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以84%的产率得到N'-(β-D-mannopyranosyl)-p-toluenesulfonohydrazide
  参考文献：
  名称：

  Protecting-Group-Free Synthesis of Glycosyl 1–Phosphates

  摘要：

  Glycosyl 1-phosphates enriched in the alpha-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.

  DOI：

  10.1021/ol3019083

文献信息

• Protecting-group-free O-glysosidation using p-toluenesulfonohydrazide and glycosyl chloride donors
  作者：Rohan J. Williams、Caroline E. Paul、Mark Nitz

  DOI：10.1016/j.carres.2013.08.019

  日期：2014.3

  A range of N '-glycosylsulfonohydrazides (GSHs) display good reactivity but poor stereoselectivity in protecting- group-free O-glycosidations when a moderate excess of the model acceptor n-decanol is employed. This stable, readily-accessed class of donor may be more tractable for the glycosylation of non-volatile acceptors than Fischer's glycosidation conditions. It is possible to generate unprotected glycosyl chlorides from GSHs in situ. In an effort to find conditions to improve glycosidation stereoselectivity, methanolysis of unprotected glucosyl chloride under halide-ion exchange conditions was examined. Relative to its tetra-O-benzyl analogue, this donor displays moderate, inverted stereoselectivity and a significantly faster reaction rate. (C) 2013 Elsevier Ltd. All rights reserved.