allyl 2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranoside | 213528-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranoside
• CAS: 213528-65-5
• 化学式: C₁₁H₁₈N₄O₅
• 分子量: 286.288
• InChiKey: PUWGZPINCOIRDU-ILAIQSSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  136.78
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 barium hydroxide octahydrate 、 potassium carbonate 、 三乙胺 、 三氟乙酸酐 、 barium(II) oxide 、 三甲基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 31.0h， 生成 (2S,3S,4R,5R,6S)-3-acetamido-1-benzyl-2-butyl-4,5-di (benzyloxy)-6-(hydroxymethyl)piperidine
  参考文献：
  名称：

  2-乙酰胺基-2-脱氧-1-亚氨基糖C-烷基和C-芳基糖苷：合成和糖苷酶抑制

  摘要：

  施陶丁格/ azawittig /格利雅/环收缩序列应用于两个d -glycopyranose衍生物轴承在C-2位乙酰氨基和叠氮基的C-6位置允许访问前所未有六元升-iminosugars Ç - GlcNAc和ManNAc模拟糖苷。格利雅（Grignard）添加物具有较高的1,2-反式非对映选择性，这强烈暗示了NHAc基团的对映体辅助作用。

  DOI：

  10.1002/ejoc.201800678
• 作为产物：
  描述：

  烯丙基 2-乙酰氨基-2-脱氧-alpha-D-吡喃葡萄糖苷 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 allyl 2-acetamido-6-azido-2,6-dideoxy-α-D-glucopyranoside
  参考文献：
  名称：

  2-乙酰胺基-2-脱氧-1-亚氨基糖C-烷基和C-芳基糖苷：合成和糖苷酶抑制

  摘要：

  施陶丁格/ azawittig /格利雅/环收缩序列应用于两个d -glycopyranose衍生物轴承在C-2位乙酰氨基和叠氮基的C-6位置允许访问前所未有六元升-iminosugars Ç - GlcNAc和ManNAc模拟糖苷。格利雅（Grignard）添加物具有较高的1,2-反式非对映选择性，这强烈暗示了NHAc基团的对映体辅助作用。

  DOI：

  10.1002/ejoc.201800678

文献信息

• Synthesis of Novel Di- and Trisaccharide Mimetics with Non-Glycosidic Amino Bridges
  作者：Janna Neumann、Saskia Weingarten、Joachim Thiem

  DOI：10.1002/ejoc.200600958

  日期：2007.3

  Synthesis of novel di- and trisaccharides using enzymatic glycosylation, Dess–Martin oxidation and reductive amination allows rapid access to the target structures. Thus, a novel class of glycomimetics was obtained having nitrogen inserted as bridging atom between two non-anomeric positions. Novel di- and trisaccharide mimetics were designed using N-acetylglucosamine as a basis structure. A third monosaccharide

  使用酶促糖基化、Dess-Martin 氧化和还原胺化合成新型二糖和三糖可以快速获得目标结构。因此，获得了一类新的糖模拟物，其中插入了氮作为两个非异头位置之间的桥接原子。使用 N-乙酰氨基葡萄糖作为基础结构设计了新型二糖和三糖模拟物。第三个单糖单元通过非天然的糖 - 糖键连接，没有异头中心的参与。它们的合成通过氧化、糖基化和还原胺化进行，只需要几个步骤，因此可以快速获得目标结构。通过 Dess-Martin 氧化和随后的还原胺化实现了新型假双糖的生成。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany,
• New Broad-Spectrum Antibacterial Amphiphilic Aminoglycosides Active against Resistant Bacteria: From Neamine Derivatives to Smaller Neosamine Analogues
  作者：Louis Zimmermann、Indrajit Das、Jérôme Désiré、Guillaume Sautrey、Vinicius Barros R. S.、Micheline El Khoury、Marie-Paule Mingeot-Leclercq、Jean-Luc Décout

  DOI：10.1021/acs.jmedchem.6b00818

  日期：2016.10.27

  of the small aminoglycoside neamine as broad spectrum antibacterial agents targeting bacterial membranes. Here, we report on the synthesis and the activity against sensitive and resistant Gram-negative and/or Gram-positive bacteria of new amphiphilic 3′,4′-dialkyl neamine derivatives and of their smaller analogues in the 6-aminoglucosamine (neosamine) series prepared from N-acetylglucosamine.

  氨基糖苷类（AGs）构成了主要的强效和广谱抗生素家族，它们通过与16S rRNA的A位点结合而干扰蛋白质的合成。几十年来，AGs的广泛临床应用通过选择耐药细菌而大大降低了其临床功效。最近，亲脂性基团与AGs的结合产生了一类新型的强效抗菌两亲氨基糖苷（AAG），其对各种敏感和耐药细菌菌株的活性均得到显着改善。我们已经确定了小氨基糖苷神经酰胺的两亲性3'，6-二烷基衍生物是靶向细菌膜的广谱抗菌剂。在这里，我们报道了新型两亲性3'对敏感和耐药革兰氏阴性和/或革兰氏阳性细菌的合成及其活性，N-乙酰氨基葡萄糖。
• Synthesis of Amino-Bridged Oligosaccharide Mimetics
  作者：Janna Neumann、Joachim Thiem

  DOI：10.1002/ejoc.200901106

  日期：2010.2

  Synthesis of amino-bridged oligosaccharides using reductive amination opens rapid access to novel glycomimetic target structures as potential ligands for the receptor protein NKR P1 of natural killer cells. Emphasis was laid on fast and facile synthetic routes. The carbonyl building blocks were easily obtained by oxidation with Dess-Martin periodinane or iodoxybenzoic acid (IBX). For the required

  使用还原胺化合成氨基桥连寡糖开辟了快速获取新的拟糖靶结构作为自然杀伤细胞受体蛋白 NKR P1 的潜在配体的途径。重点放在快速简便的合成路线上。通过用戴斯-马丁高碘烷或碘氧基苯甲酸 (IBX) 氧化很容易获得羰基结构单元。对于所需的氨基官能化单元，叠氮化物前体的还原是有利的，并且通过随后的还原胺化实现了新型寡糖的生成。目标糖类结构的特征是在两个非异头位置之间插入一个桥接氮原子，并包括一个异头位置。
• Synthesis of linked carbohydrates and evaluation of Their binding for 16S RNA by mass spectrometry
  作者：Baogen Wu、Jun Yang、Dale Robinson、Steve Hofstadler、Rich Griffey、Eric E. Swayze、Yun He

  DOI：10.1016/j.bmcl.2003.09.005

  日期：2003.11

  A library of linked molecules were synthesized from the common sugar moieties existing in the natural amino glycosides. These linked molecules were screened against bacterial 16S RNA for their binding affinity using a mass spectrometry-based technology. Some of these compounds exhibited low micromolar affinity and could serve as leads for further development as antibacterial agents. (C) 2003 Published by Elsevier Ltd.
• A Library Approach to the Discovery of Small Molecules That Recognize RNA:  Use of a 1,3-Hydroxyamine Motif as Core
  作者：Chi-Huey Wong、Martin Hendrix、David D. Manning、Christoph Rosenbohm、William A. Greenberg

  DOI：10.1021/ja980826p

  日期：1998.8.1

  A library of compounds based upon an aminoglucopyranoside core has been developed and screened for binding to RNA and specifically to 16S ribosomal RNA. The title molecules simplify the complexity of naturally occurring aminoglycoside antibiotics by embodying a putative recognition motif found within these structures, namely, a 1,3-hydroxyamine. The core pyranoside bearing the hydroxyamine motif was structurally varied at two points through a combinatorial approach utilizing acylation and reductive amination protocols. The aminoglycoside mimetics were screened in an automated assay based upon surface plasmon resonance (SPR), and some were found effective at binding a 27-nucleotide model (AS-wt) of A-site 16S RNA as well as a drug-resistant mutant RNA in the micromolar range.