N-octyl-N-trifluoroacetyl-2,3,6-tri-O-benzoyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine | 442852-06-4

• 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: N-octyl-N-trifluoroacetyl-2,3,6-tri-O-benzoyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
• CAS: 442852-06-4
• 化学式: C₃₈H₄₀F₃NO₈
• 分子量: 695.733
• InChiKey: IUDGJDGLZVDDKY-FYZVQMPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  50.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  119.44
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-octyl-N-trifluoroacetyl-2,3,6-tri-O-benzoyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 在 4 A molecular sieve 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 4-O-(β-D-galactopyranosyl)-N-octyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
  参考文献：
  名称：

  Chemical Modification of the β-Glucocerebrosidase Inhibitor N-Octyl-β-valienamine: Synthesis and Biological Evaluation of 4-Epimeric and 4-O-(β-?-Galactopyranosyl) Derivatives

  摘要：

  N-Octyl-beta-valienemine (1), a potent beta-glucocerebrosidase inhibitor, was chemically transformed into two biologically interesting compounds: the 4-epimer 2, beta-galacto-type N-octyl-valienamine, and the 4-O-(beta-D-galactopyranosyl) derivative 3, a carba-lactosylceramide analogue. The former, interestingly, could be demonstrated to act as a very effective inhibitor (IC50=0.3 muM) of human beta-galactosidase. The latter exhibited moderate inhibitory activity (IC50=20 muM) against beta-glucocerebrosidase (mouse liver). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00005-6
• 作为产物：
  描述：

  N-octyl-N-trifluoroacetyl-2,3-di-O-benzoyl-4,6-O-benzylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 在 溶剂黄146 作用下， 以 吡啶 、 水 为溶剂， 反应 3.5h， 生成 N-octyl-N-trifluoroacetyl-2,3,6-tri-O-benzoyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
  参考文献：
  名称：

  Chemical Modification of the β-Glucocerebrosidase Inhibitor N-Octyl-β-valienamine: Synthesis and Biological Evaluation of 4-Epimeric and 4-O-(β-?-Galactopyranosyl) Derivatives

  摘要：

  N-Octyl-beta-valienemine (1), a potent beta-glucocerebrosidase inhibitor, was chemically transformed into two biologically interesting compounds: the 4-epimer 2, beta-galacto-type N-octyl-valienamine, and the 4-O-(beta-D-galactopyranosyl) derivative 3, a carba-lactosylceramide analogue. The former, interestingly, could be demonstrated to act as a very effective inhibitor (IC50=0.3 muM) of human beta-galactosidase. The latter exhibited moderate inhibitory activity (IC50=20 muM) against beta-glucocerebrosidase (mouse liver). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00005-6