((3aS,4R,9aR,9bS)-2,8-Diphenyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-octyl-carbamic acid tert-butyl ester | 442852-09-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: ((3aS,4R,9aR,9bS)-2,8-Diphenyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-octyl-carbamic acid tert-butyl ester
• CAS: 442852-09-7
• 化学式: C₃₄H₄₅NO₆
• 分子量: 563.734
• InChiKey: LEMLQISPXDGIEF-VNRGWSAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.49
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.46
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ((3aS,4R,9aR,9bS)-2,8-Diphenyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-octyl-carbamic acid tert-butyl ester 在 对甲苯磺酸 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 N-octyl-N-tert-butoxycarbonyl-2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl-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-tert-butoxycarbonyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 在 对甲苯磺酸 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 ((3aS,4R,9aR,9bS)-2,8-Diphenyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-octyl-carbamic acid tert-butyl ester
  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