N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-carboxyethylmethylene thiourea | 198271-89-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-carboxyethylmethylene thiourea
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5R)-3,4-dibenzoyloxy-5-[(2-ethoxy-2-oxoethyl)carbamothioylamino]oxolan-2-yl]ethyl] benzoate
• CAS: 198271-89-5
• 化学式: C₃₉H₃₆N₂O₁₁S
• 分子量: 740.788
• InChiKey: AXECTFGSBHYYQQ-SSWJQGRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  197
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-carboxyethylmethylene thiourea 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到N-β-D-galactofuranosyl-5-oxo-imidazolidine-2-thione
  参考文献：
  名称：

  Synthesis of β-d-galactofuranosyl nucleoside analogues. A new type of β-d-galactofuranosidase inhibitor

  摘要：

  The development of beta -D-galactofuranosidase inhibitors provides a good chemotherapeutic target for treatment of major human diseases, because beta -D-galactofuranose is a constituent of important pathogen microorganisms but is absent in mammals. With this purpose we have prepared beta -D-galactofuranosyl nucleoside analogues, derived by the addition of nucleophiles to perbenzoylated beta -D-galactofuranosyl isothiocyanate, a compound previously prepared in this laboratory. N-beta -D-Galactofuratlosyl-O-ethylthiourethane N-beta -D-galactofuranosyl-4-oxoimidazolidi N-beta -D-galactofuranosyl-4-imidazoline-2-thione, and N-beta -D-galactofuranosyl-4-methoxyimidazolidine-2-thione, were prepared. The biological assays showed that imidazoline and imidazolidine-2-thione derivatives act as a new type of exo beta -D-galactofuranosidase inhibitor. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00146-x
• 作为产物：
  描述：

  2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl bromide 在 Etifelmin 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 5.0h， 生成 N-(2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl)-N'-carboxyethylmethylene 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