(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-mannopyranosyl)-4-(3-nitrophenyl)but-3-en-2-one | 1042966-28-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-mannopyranosyl)-4-(3-nitrophenyl)but-3-en-2-one
• 英文别名: 3-nitrophenyl 2-oxobut-3-enylmannopyranoside；[(2R,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-[(E)-4-(3-nitrophenyl)-2-oxobut-3-enyl]oxan-2-yl]methyl acetate
• CAS: 1042966-28-8
• 化学式: C₂₄H₂₇NO₁₂
• 分子量: 521.478
• InChiKey: RHTGOPKTUAGTTA-OIYCGUTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  177
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-mannopyranosyl)-4-(3-nitrophenyl)but-3-en-2-one 在 tin(II) chloride dihdyrate 作用下， 以 乙醇 为溶剂， 以68%的产率得到(E)-4-(3-aminophenyl)-1-[1′-deoxy-2′,3′,4′,6′-tetra-O-acetyl-β-D-mannopyranos-1′-yl]but-3-en-2-one
  参考文献：
  名称：

  Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

  摘要：

  A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the C-linked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC50 values in micromolar range and low cytotoxicity offering new HITS for further exploration.

  DOI：

  10.1021/ml500211c
• 作为产物：
  描述：

  5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-D-galacto-non-2-ulose 、 间硝基苯甲醛 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以70%的产率得到(E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-mannopyranosyl)-4-(3-nitrophenyl)but-3-en-2-one
  参考文献：
  名称：

  Aldol reaction of β-C-glycosylic ketones: synthesis of C-(E)-cinnamoyl glycosylic compounds as precursors for new biologically active C-glycosides

  摘要：

  A series of beta-C-glycosylic ketones were prepared starting from D-glucose, D-xylose, D-mannose, and cellobiose. The beta-C-glycosylic ketones on aldol condensation with different aromatic aldehydes in the presence of a suitable organocatalyst led to the formation of respective C-(E)-cinnamoyl glycosides stereoselectively in good yields as precursors for the synthesis of biologically active compounds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.04.021