phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside | 874908-94-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
• 英文别名: [(2R,3R,6R)-3-acetyloxy-6-[(1,3-dioxoisoindol-2-yl)methoxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 874908-94-8
• 化学式: C₁₉H₁₉NO₈
• 分子量: 389.362
• InChiKey: ROQJQHMRJVOZPA-ZACQAIPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 以75%的产率得到phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hexopyranoside
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides

  摘要：

  3,4,6-Tri-O-acetyl-D -gal actal, 3,4,6-tri-O-acetyl-D-glucal and 3,6,2',3',46'-hexa-0-acetyl-D-lactaI were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivative was used, a non-Ferrier rearrangement product was also isolated as a minor product under classical Ferrier conditions. Phthalimidomethyl deoxy glycosides were readily prepared by hydrogenation of the unsaturated glycosides. Following deacetylation, the anti-inflammatory activities of these compounds were tested on mice and three were found to possess potent activity compared to hydrocortisone sodium succinate (HSS). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.009
• 作为产物：
  描述：

  N-羟甲基邻苯二甲酰亚胺 、 D-三乙酰半乳糖烯 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 以60%的产率得到phthalimidomethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides

  摘要：

  3,4,6-Tri-O-acetyl-D -gal actal, 3,4,6-tri-O-acetyl-D-glucal and 3,6,2',3',46'-hexa-0-acetyl-D-lactaI were reacted with N-hydroxymethylphthalimide and boron trifluoride etherate to produce the corresponding phthalimidomethyl unsaturated glycosides via Ferrier rearrangement. When the galactal derivative was used, a non-Ferrier rearrangement product was also isolated as a minor product under classical Ferrier conditions. Phthalimidomethyl deoxy glycosides were readily prepared by hydrogenation of the unsaturated glycosides. Following deacetylation, the anti-inflammatory activities of these compounds were tested on mice and three were found to possess potent activity compared to hydrocortisone sodium succinate (HSS). (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.03.009