(1R)-1-C-allyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol | 1354483-32-1

• 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: (1R)-1-C-allyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol
• 英文别名: α-C-allyl-2,3,4-tri-O-benzyl-1-deoxynojirimycin
• CAS: 1354483-32-1
• 化学式: C₂₉H₃₃NO₃
• 分子量: 443.586
• InChiKey: PTWAJNGEWPEYNP-GKQHHHCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  33.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  39.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R)-1-C-allyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol 在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 18.08h， 生成 α-C-allyl-3,4-di-O-benzyl-1-deoxyxylonojirimycin
  参考文献：
  名称：

  Site-Selective Debenzylation of C-Allyl Iminosugars Enables Their Stereocontroled Structure Diversification at the C-2 Position

  摘要：

  A C-2 regioselective debenzylative cycloetherification/reductive elimination sequence applied to perbenzylated C-allyl iminosugars is described. This NIS/TMSOTf-triggered deprotection was successfully applied to five-, six-, and seven-membered C-allyl iminosugars including 1,2 cis and 1,2 trans stereoisomers. It allows rapid introduction of structural diversity at the key C-2 position in a stereoselective manner exploiting the anchimeric assistance of the intracyclic N-benzyl group, giving access to the 2-acetamido and 2-fluoro d-gluco configured C-allyl iminosugars and to the epimeric d-manno derivative.

  DOI：

  10.1021/acs.orglett.9b01712
• 作为产物：
  描述：

  (1R)-1-C-allyl-N-naphth-2-ylmethyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol 在 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以86%的产率得到(1R)-1-C-allyl-2,3,4-tri-O-benzyl-1,5-dideoxy-1,5-imino-D-xylitol
  参考文献：
  名称：

  叠氮化物武装的α-1- C-烷基-亚氨基-d-木糖醇衍生物的合成作为制备氨基糖点击偶联物的关键组成部分

  摘要：

  叠氮化物-武装α-1- Ç -烷基-亚氨基- d -木糖醇衍生物已通过烯烃交叉复分解的方式被有效地制备在八至九的步骤和在19％，从2,3,4-总收率26％三- ø苄基d -xylopyranose。还报道了使用DDQ在CH 2 Cl 2 -H 2 O（18：1）中优化N -NAP保护的叔胺的裂解条件。合成的亚氨基糖将通过Cu（I）催化的叠氮化物-炔烃环加成反应，被用作生物感兴趣的多价亚氨基糖合成的关键组成部分。

  DOI：

  10.1080/07328303.2011.610544

文献信息

• Synthesis and Evaluation of Lipophilic Aza-C-glycosides as Inhibitors of Glucosylceramide Metabolism
  作者：Tom Wennekes、Richard J. B. H. N. van den Berg、Thomas J. Boltje、Wilma E. Donker-Koopman、Bastiaan Kuijper、Gijsbert A. van der Marel、Anneke Strijland、Carlo P. Verhagen、Johannes M. F. G. Aerts、Herman S. Overkleeft

  DOI：10.1002/ejoc.200901208

  日期：2010.3

  The structure–activity relationship of lipophilic aza-C-glycosides as inhibitors of the three enzymes of glucosylceramide metabolism is investigated. A library of β-aza-C-glycosides was synthesized with variations in N-alkylation and the linker length/type to the lipophilic moiety. A cross-metathesis reaction was used to prepare a second library of α-aza-C-glycosides with D-gluco, L-ido and D-xylo

  研究了亲脂性氮杂-C-糖苷作为葡萄糖神经酰胺代谢三种酶抑制剂的构效关系。合成了一个 β-氮杂-C-糖苷库，其中 N-烷基化和亲脂性部分的接头长度/类型有所不同。使用交叉复分解反应制备第二个 α-氮杂-C-糖苷库，其中 D-葡萄糖、L-ido 和 D-木亚氨基糖核心具有类似的接头变异。对两个文库的评估均未发现葡萄糖神经酰胺合酶的有效或选择性抑制剂。然而，发现 β-aza-C-glycoside 43 是 β-glucosidase 2 的选择性抑制剂。葡萄糖脑苷脂酶的选择性抑制剂。
• Iminosugars as a new class of cholinesterase inhibitors
  作者：Camille Decroocq、Fabien Stauffert、Olivier Pamlard、Farah Oulaïdi、Estelle Gallienne、Olivier R. Martin、Catherine Guillou、Philippe Compain

  DOI：10.1016/j.bmcl.2014.12.071

  日期：2015.2

  To further extend the scope of iminosugar biological activity, a systematic structure-activity relationship investigation has been performed by synthesizing and evaluating as cholinesterase inhibitors a library of twenty-three iminoalditols with different substitutions and stereochemistry patterns. These compounds have been evaluated in vitro for the inhibition of cholinesterases (different sources of acetylcholinesterase and butyrylcholinesterase). Some compounds have IC50 values in the micromolar range and display significant inhibition selectivity for butyrylcholinesterase over acetylcholinesterase. These are the first examples of iminosugar-based inhibitors of cholinesterases. (C) 2015 Elsevier Ltd. All rights reserved.