(2R,3R,4R,5S,6R)-6-benzylamino-1,3,4,5-tetrabenzyloxynon-8-en-2-ol | 292165-63-0

• 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: (2R,3R,4R,5S,6R)-6-benzylamino-1,3,4,5-tetrabenzyloxynon-8-en-2-ol
• 英文别名: (1R)-1-C-allyl-2,3,4,6-tetra-O-benzyl-1-benzylamino-1-deoxy-D-glucitol；(2R,3R,4R,5S,6R)-6-(benzylamino)-1,3,4,5-tetrakis(phenylmethoxy)non-8-en-2-ol
• CAS: 292165-63-0
• 化学式: C₄₄H₄₉NO₅
• 分子量: 671.877
• InChiKey: KKRDRBUAAYGOFK-LUKFIAJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  50
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S,6R)-6-benzylamino-1,3,4,5-tetrabenzyloxynon-8-en-2-ol 在 trifluoromethanesulfonic acid anhydride 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以52%的产率得到(2R,3S,4R,5R,6S)-N-benzyl-3,4,5-tribenzyloxy-6-benzyloxymethyl-2-(2-propenyl)piperidine
  参考文献：
  名称：

  糖胺上的格氏反应合成氮杂糖

  摘要：

  吡咯烷5a-b以及哌啶10a，b和15是通过在糖基胺上进行格氏反应合成的，该糖基胺很容易从母体糖和伯胺中获得，然后用三氟甲磺酸酐环化。

  DOI：

  10.1016/0040-4020(95)00151-w
• 作为产物：
  描述：

  N-benzyl-2,3,4,6-tetra-O-benzyl-D-glucopyranosylamine 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 反应 48.0h， 以2.54 g的产率得到(2R,3R,4R,5S,6R)-6-benzylamino-1,3,4,5-tetrabenzyloxynon-8-en-2-ol
  参考文献：
  名称：

  Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors

  摘要：

  A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-L-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the D-gluco and D-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.027

文献信息

• Synthesis of azasugars by Grignard reaction on glycosylamines
  作者：Laura Cipolla、Luigi Lay、Francesco Nicotra、Cristina Pangrazio、Luigi Panza

  DOI：10.1016/0040-4020(95)00151-w

  日期：1995.4

  Pyrrolidines 5a-b, and piperidines 10a,b and 15, were synthesised by Grignard reaction on a glycosylamine, easily obtained from the parent sugar and a primary amine, followed by cyclization with triflic anhydride.

  吡咯烷5a-b以及哌啶10a，b和15是通过在糖基胺上进行格氏反应合成的，该糖基胺很容易从母体糖和伯胺中获得，然后用三氟甲磺酸酐环化。
• Cipolla, Laura; Nicotra, Francesco; Pangrazio, Cristina, Gazzetta Chimica Italiana, 1996, vol. 126, # 10, p. 663 - 666
  作者：Cipolla, Laura、Nicotra, Francesco、Pangrazio, Cristina

  DOI：——

  日期：——
• Synthesis of new β-1-C-alkylated imino-l-iditols: A comparative study of their activity as β-glucocerebrosidase inhibitors
  作者：Wojciech Schönemann、Estelle Gallienne、Philippe Compain、Kyoko Ikeda、Naoki Asano、Olivier R. Martin

  DOI：10.1016/j.bmc.2010.02.027

  日期：2010.4

  A short synthesis of new beta-1-C-alkyl-1,5-dideoxy-1,5-imino-L-iditols by means of the diastereoselective addition of Grignard reagents onto a glucopyranosylamine is described. These compounds were evaluated as beta-glucocerebrosidase inhibitors and their activity was compared with that of related iminosugar derivatives in the D-gluco and D-xylo series. The results allowed us to conclude on the influence of the hydroxymethyl moiety and of the piperidine-ring conformation on the inhibitory activity. (C) 2010 Elsevier Ltd. All rights reserved.