1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-5-yl)-4-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-5-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-1,2,3-1H-triazole | 1263036-25-4

• 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-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-5-yl)-4-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-5-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-1,2,3-1H-triazole
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-[[5-[[(2R,3S,6S)-3-acetyloxy-2-(acetyloxymethyl)-3,6-dihydro-2H-pyran-6-yl]oxymethyl]-1-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]triazol-4-yl]methoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1263036-25-4
• 化学式: C₃₈H₄₉N₃O₂₁
• 分子量: 883.815
• InChiKey: DCWJYZDUIUKYIB-BLDDPTJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  62
• 可旋转键数：
  26
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  287
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-5-yl)-4-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-5-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-1,2,3-1H-triazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以79%的产率得到1-(β-D-glucopyranos-5-yl)-4-(2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-5-(2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-1,2,3-1H-triazole
  参考文献：
  名称：

  Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors

  摘要：

  An efficient synthesis of novel 1,2,3-1H-triazolyl glycohybrids with two or more than two sugar units or a chromenone moiety via copper-catalysed azide-alkyne cycloaddition (CuAAC), a 1,3-dipolar cycloaddition of glycosyl azides to 2,3-unsaturated alkynyl glycosides or propargyloxy coumarins is described. The synthesised glycohybrids were screened for their a-glucosidase, glycogen phosphorylase and glucose-6-phosphatase inhibitory activities. A few of the glycohybrids showed promising inhibitory activities against these enzymes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.10.017
• 作为产物：
  描述：

  but-2-yne-1,4-diyl bis(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside) 、 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 以 甲苯 为溶剂， 以71%的产率得到1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-5-yl)-4-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-5-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranos-1-yloxymethyl)-1,2,3-1H-triazole
  参考文献：
  名称：

  Application of click chemistry towards an efficient synthesis of 1,2,3-1H-triazolyl glycohybrids as enzyme inhibitors

  摘要：

  An efficient synthesis of novel 1,2,3-1H-triazolyl glycohybrids with two or more than two sugar units or a chromenone moiety via copper-catalysed azide-alkyne cycloaddition (CuAAC), a 1,3-dipolar cycloaddition of glycosyl azides to 2,3-unsaturated alkynyl glycosides or propargyloxy coumarins is described. The synthesised glycohybrids were screened for their a-glucosidase, glycogen phosphorylase and glucose-6-phosphatase inhibitory activities. A few of the glycohybrids showed promising inhibitory activities against these enzymes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.10.017