N-phenacyl-N'-(3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxohexopyranosyl)thiourea | 136962-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-phenacyl-N'-(3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxohexopyranosyl)thiourea
• 英文别名: [(2R,3R,4R,6R)-3,4-diacetyloxy-6-(phenacylcarbamothioylamino)oxan-2-yl]methyl acetate
• CAS: 136962-82-8
• 化学式: C₂₁H₂₆N₂O₈S
• 分子量: 466.512
• InChiKey: FRLDQLPUGHQWBX-UAFMIMERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  32.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  2-氨基苯乙酮盐酸盐 、 3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxohexopyranosyl isothiocyanate 在 碳酸氢钠 作用下， 生成 N-phenacyl-N'-(3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxohexopyranosyl)thiourea
  参考文献：
  名称：

  Preparation and properties of 2-deoxyglycosyl isothiocyanates

  摘要：

  The syntheses of 3,4,6-tri-O-acetyl-2- deoxy-alpha and beta-D-arabino (D-lyxo)hexopyranosyl isothiocyanates (2, 3, 6, 7) and 4,6-di-O-acetyl-3-bromo-2,3-dideoxy-beta-D-arabinohexopyranosyl isothiocyanate (5) are reported. Treatments of 2,3,6, and 7 with phenacylamine hydrochloride and of 2 with aminoacetone hydrochloride gave the corresponding N-phenacyl (acetylmethyl)-N'-(2-deoxyglycosyl)-thioureas (8-12). The N-nucleoside analogues 5-methyl-1-(3',4',6'-tri-O- acetyl-2'-deoxy-alpha-D-arabinohexopyranosyl)-4-imidazoline-2-thione (13) was obtained by cyclodehydration of the thiourea 12.

  DOI：

  10.1016/s0040-4020(01)86530-3

文献信息

• Preparation and properties of 2-deoxyglycosyl isothiocyanates
  作者：José Fuentes、M.Angeles Pradera、Inmaculada Robina

  DOI：10.1016/s0040-4020(01)86530-3

  日期：1991.7

  The syntheses of 3,4,6-tri-O-acetyl-2- deoxy-alpha and beta-D-arabino (D-lyxo)hexopyranosyl isothiocyanates (2, 3, 6, 7) and 4,6-di-O-acetyl-3-bromo-2,3-dideoxy-beta-D-arabinohexopyranosyl isothiocyanate (5) are reported. Treatments of 2,3,6, and 7 with phenacylamine hydrochloride and of 2 with aminoacetone hydrochloride gave the corresponding N-phenacyl (acetylmethyl)-N'-(2-deoxyglycosyl)-thioureas (8-12). The N-nucleoside analogues 5-methyl-1-(3',4',6'-tri-O- acetyl-2'-deoxy-alpha-D-arabinohexopyranosyl)-4-imidazoline-2-thione (13) was obtained by cyclodehydration of the thiourea 12.