1-ethoxy(phenyl)thiophosphoryl-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)thiosemicarbazide | 1173986-18-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-ethoxy(phenyl)thiophosphoryl-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)thiosemicarbazide
• 英文别名: [(3R,4S,5R,6R)-4,5-diacetyloxy-6-[[[ethoxy(phenyl)phosphinothioyl]amino]carbamothioylamino]oxan-3-yl] acetate
• CAS: 1173986-18-9
• 化学式: C₂₀H₂₈N₃O₈PS₂
• 分子量: 533.563
• InChiKey: BVLMHWCUKNENLI-UHFKPTSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  198
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-ethoxy(phenyl)thiophosphoryl-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)thiosemicarbazide 、 溴乙酸乙酯 以 二氯甲烷 为溶剂， 反应 12.0h， 以63%的产率得到3-ethoxy(phenyl)thiophosphorylamido-2-(2',3',4'-tri-O-acetyl-β-D-xylopyranosyl-1'-imino)thiazolidine-4-one
  参考文献：
  名称：

  Regioselective synthesis of novel 3-alkoxy (phenyl) thiophosphorylamido-2-(per-O-acetylglycosyl-1′-imino)thiazolidine-4-one derivatives from O-alkyl N4-glycosyl(thiosemicarbazido)phosphonothioates

  摘要：

  A series of 3-alkoxy(phenyl)thiophosphorylamido-2-(per-O-acetylglycosyl-1'-imino)thiazolidine-4-one derivatives were prepared by the reaction of 1-alkoxy(phenyl)thiophosphoryl-4-(per-O-acetylglycosyl) thiosemicarbazides with ethyl bromoacetate. H-1/C-13 HMBC measurements corroborated by X-ray crystallographic results revealed the exclusive regioselectivity of these ring closures toward the N-2 position of the thiosemicarbazide moiety. The bioactivity data of 3a-k suggest that the thiazolidine-4-one ring is critical for the herbicidal and fungicidal activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.027
• 作为产物：
  描述：

  2,3,4,-tri-O-Acetyl-β-D-xylopyranosyl isothiocyanate 、 [ethoxy(phenyl)phosphinothioyl]hydrazine 以 乙腈 为溶剂， 反应 2.0h， 以73%的产率得到1-ethoxy(phenyl)thiophosphoryl-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)thiosemicarbazide
  参考文献：
  名称：

  Regioselective synthesis of novel 3-alkoxy (phenyl) thiophosphorylamido-2-(per-O-acetylglycosyl-1′-imino)thiazolidine-4-one derivatives from O-alkyl N4-glycosyl(thiosemicarbazido)phosphonothioates

  摘要：

  A series of 3-alkoxy(phenyl)thiophosphorylamido-2-(per-O-acetylglycosyl-1'-imino)thiazolidine-4-one derivatives were prepared by the reaction of 1-alkoxy(phenyl)thiophosphoryl-4-(per-O-acetylglycosyl) thiosemicarbazides with ethyl bromoacetate. H-1/C-13 HMBC measurements corroborated by X-ray crystallographic results revealed the exclusive regioselectivity of these ring closures toward the N-2 position of the thiosemicarbazide moiety. The bioactivity data of 3a-k suggest that the thiazolidine-4-one ring is critical for the herbicidal and fungicidal activities. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.03.027