3-methoxy(phenyl)thiophosphorylamido-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-1'-imino)thiazolidine-4-one | 1173986-24-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methoxy(phenyl)thiophosphorylamido-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-1'-imino)thiazolidine-4-one
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[3-[[methoxy(phenyl)phosphinothioyl]amino]-4-oxo-1,3-thiazolidin-2-ylidene]amino]oxan-2-yl]methyl acetate
• CAS: 1173986-24-7
• 化学式: C₂₄H₃₀N₃O₁₁PS₂
• 分子量: 631.621
• InChiKey: HUWHIYILOYTEMM-XSLSSXFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  168.36
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  1-methoxy(phenyl)thiophosphoryl-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)thiosemicarbazide 、 溴乙酸乙酯 以 二氯甲烷 为溶剂， 反应 12.0h， 以61%的产率得到3-methoxy(phenyl)thiophosphorylamido-2-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-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