N-octyl-N-tert-butoxycarbonyl-4,6-O-benzylidene-2,3-di-O-methoxymethyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine | 442851-98-1

• 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-tert-butoxycarbonyl-4,6-O-benzylidene-2,3-di-O-methoxymethyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
• 英文别名: N-octyl-N-tert-butoxycarbonyl-4,6-O-benzylidene-2,3-di-O-methoxymethyl-5a-carba-β-D-xylo-hexo-5(5a)-enopyranosylamine
• CAS: 442851-98-1
• 化学式: C₃₁H₄₉NO₈
• 分子量: 563.732
• InChiKey: ZTQXMOSIOJGEGM-MJXUZWQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  84.92
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-octyl-N-tert-butoxycarbonyl-4,6-O-benzylidene-2,3-di-O-methoxymethyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 在 4 A molecular sieve 、 L-Selectride 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-octyl-N-tert-butoxycarbonyl-2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl-5a-carba-α-L-arabino-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 、 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 9.17h， 生成 N-octyl-N-tert-butoxycarbonyl-4,6-O-benzylidene-2,3-di-O-methoxymethyl-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

文献信息

• CARBA-SUGAR AMINE DERIVATIVES AND TREATMENTS FOR DISORDER OF GLYCOLIPID METABOLISM CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：SEIKAGAKU CORPORATION

  公开号：EP1433776B1

  公开（公告）日：2011-01-19