1-diethoxythiophosphoryl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide | 414861-86-2

• 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: 1-diethoxythiophosphoryl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(diethoxyphosphinothioylamino)carbamothioylamino]oxan-2-yl]methyl acetate
• CAS: 414861-86-2
• 化学式: C₁₉H₃₂N₃O₁₁PS₂
• 分子量: 573.582
• InChiKey: BKKJLPUWENANDV-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  233
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1-diethoxythiophosphoryl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide 、 溴乙酸乙酯 以 二氯甲烷 为溶剂， 反应 12.0h， 以48%的产率得到3-diethoxythiophosphorylamido-2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-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：

  O,O-diethyl phosphorohydrazidothioate 、 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 以 乙腈 为溶剂， 反应 2.0h， 以87%的产率得到1-diethoxythiophosphoryl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)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

文献信息

• 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
  作者：Yu Xin Li、Hao An Wang、Xiao Ping Yang、Hai Ying Cheng、Zhi Hong Wang、Yi Ming Li、Zheng Ming Li、Su Hua Wang、Dong Wen Yan

  DOI：10.1016/j.carres.2009.03.027

  日期：2009.7

  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.