(2R,3R,4S,5R,6R)-1-benzyl-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)azepan-6-ol | 943135-52-2

• 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,4S,5R,6R)-1-benzyl-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)azepan-6-ol
• 英文别名: (3R,4R,5S,6R,7R)-1-benzyl-4,5,6-tris(phenylmethoxy)-7-(phenylmethoxymethyl)azepan-3-ol
• CAS: 943135-52-2
• 化学式: C₄₂H₄₅NO₅
• 分子量: 643.823
• InChiKey: SCYPXPMZQLFNGN-MHBOMZLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6R)-1-benzyl-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)azepan-6-ol 在 甲基磺酰氯 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (1S,3R,4R,5R,8R)-2-benzyl-4,8-bis(benzyloxy)-3-(benzyloxymethyl)-6-oxa-2-azabicyclo[3.2.1]octane
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors of Two Ether-Bridged Iminosugars

  摘要：

  Two bicyclic iminosugars have been synthesized from polyhydroxylated azepanes by ring isomerization followed by debenzylative cyclization. Their conformations have been studied by NMR and molecular modeling and their glycosidase inhibition profiles were determined. They both adopt a chair conformation for the piperidine ring and display weak inhibition on alpha-glucosidases.

  DOI：

  10.1080/07328303.2011.630547
• 作为产物：
  描述：

  (2R,3R,4R,5R,6R)-N-benzyloxycarbonyl-2-benzyloxymethyl-3,4-dibenzyloxy-5,6-dihydroxy-azepane 在 Lindlar's catalyst 吡啶 、 4 Angstroem MS 、 四丁基氟化铵 、 氢气 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4S,5R,6R)-1-benzyl-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)azepan-6-ol
  参考文献：
  名称：

  Access to Homoglyconojirimycins via Ring Isomerisation of Penta­hydroxylated Azepanes

  摘要：

  N-苄基五羟基氮杂环庚烷在对氮原子的β羟基进行梅斯化时，会经历环异构化，涉及一个邻近氮原子的参与，形成一个短暂的氮杂环烷类中间体，该中间体被氯捕获。最终得到的氯甲基四羟基哌啶已被转化为相应的同糖酸酶抑制剂。

  DOI：

  10.1055/s-2007-973884

文献信息

• γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP
  作者：Y. Jagadeesh、A. T. Tran、B. Luo、N. Auberger、J. Désiré、S. Nakagawa、A. Kato、Y. Zhang、M. Sollogoub、Y. Blériot

  DOI：10.1039/c5ob00050e

  日期：——

  A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to alpha-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a gamma-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.

  已经合成了一系列五羟基化的吡咯烷，其显示出五个连续的立体生成中心，并且是α-葡糖苷酶抑制剂homoDMDP的差向异构体。关键步骤涉及将γ-氨基醇重排应用于多羟基化的沸腾石。这些五元亚氨基糖表现出对糖苷酶的微摩尔抑制作用。
• Access to Homoglyconojirimycins via Ring Isomerisation of Penta­hydroxylated Azepanes
  作者：Yves Blériot、Tao Liu、Yongmin Zhang

  DOI：10.1055/s-2007-973884

  日期：2007.4

  N-Benzyl pentahydroxyazepanes undergo ring isomerization during mesylation of the hydroxyl group β to the nitrogen via a neighboring nitrogen participation involving a transient aziridinium species which is trapped by chlorine. The resulting chloro­methyl tetrahydroxypiperidines have been converted into the corresponding homoglyconojirimycins.

  N-苄基五羟基氮杂环庚烷在对氮原子的β羟基进行梅斯化时，会经历环异构化，涉及一个邻近氮原子的参与，形成一个短暂的氮杂环烷类中间体，该中间体被氯捕获。最终得到的氯甲基四羟基哌啶已被转化为相应的同糖酸酶抑制剂。
• Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors of Two Ether-Bridged Iminosugars
  作者：Bo Luo、Filipa Marcelo、Jérôme Désiré、Yongmin Zhang、Matthieu Sollogoub、Atsushi Kato、Isao Adachi、F. Javier Cañada、Jesús Jiménez-Barbero、Yves Blériot

  DOI：10.1080/07328303.2011.630547

  日期：2011.9.1

  Two bicyclic iminosugars have been synthesized from polyhydroxylated azepanes by ring isomerization followed by debenzylative cyclization. Their conformations have been studied by NMR and molecular modeling and their glycosidase inhibition profiles were determined. They both adopt a chair conformation for the piperidine ring and display weak inhibition on alpha-glucosidases.