1-diethoxythiophosphoryl-4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl]thiosemicarbazide | 562070-25-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-diethoxythiophosphoryl-4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl]thiosemicarbazide
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[(diethoxyphosphinothioylamino)carbamothioylamino]-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 562070-25-1
• 化学式: C₃₁H₄₈N₃O₁₉PS₂
• 分子量: 861.837
• InChiKey: SHTRAUUMBIDASD-KJRJSTJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  56
• 可旋转键数：
  25
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  331
• 氢给体数：
  3
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  1-diethoxythiophosphoryl-4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl]thiosemicarbazide 、 溴乙酸乙酯 以 二氯甲烷 为溶剂， 反应 12.0h， 以35%的产率得到3-diethoxythiophosphorylamido-2-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-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 、 2,3,6,2',3',4'6'-hepta-O-acetyl-β-D-lactopyranosyl isothiocianate 以 乙腈 为溶剂， 反应 2.0h， 以67%的产率得到1-diethoxythiophosphoryl-4-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-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