N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-2(R)-hydroxypropyl thiourea

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-2(R)-hydroxypropyl thiourea
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-[[(2R)-2-hydroxypropyl]carbamothioylamino]oxolan-2-yl]ethyl] benzoate
• 化学式: C₃₈H₃₆N₂O₁₀S
• 分子量: 712.777
• InChiKey: LLZXDJWUYRLTHT-YTLYUODFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  191
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl bromide 以 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-2(R)-hydroxypropyl thiourea
  参考文献：
  名称：

  Reactions of per-O-benzoyl-β-D-Galf isothiocyanate, a chiral resolving agent

  摘要：

  Tetra-O-benzoyl-beta-D-galactofuranosyl isothiocyanate (1) was readily prepared (90% yield) from per-O-benzoyl-D-galactofuranose, via the glycosyl bromide. Reaction of 1 with alcohols, amines and amino acids afforded a variety of glycosylthiourethanes and glycosylthioureides. The isothiocyanate 1 showed to be useful as a chiral resolving agent. The resolution of racemic primary and secondary amines and aminoalcohols was readily accomplished, in analytical and preparative scale, by condensation of such compounds with 1. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10070-9

文献信息

• Reactions of per-O-benzoyl-β-D-Galf isothiocyanate, a chiral resolving agent
  作者：Carla Marino、Oscar Varela、Rosa M. de Lederkremer

  DOI：10.1016/s0040-4020(97)10070-9

  日期：1997.11

  Tetra-O-benzoyl-beta-D-galactofuranosyl isothiocyanate (1) was readily prepared (90% yield) from per-O-benzoyl-D-galactofuranose, via the glycosyl bromide. Reaction of 1 with alcohols, amines and amino acids afforded a variety of glycosylthiourethanes and glycosylthioureides. The isothiocyanate 1 showed to be useful as a chiral resolving agent. The resolution of racemic primary and secondary amines and aminoalcohols was readily accomplished, in analytical and preparative scale, by condensation of such compounds with 1. (C) 1997 Elsevier Science Ltd.