5,6,3',4'-tetra-O-acetyl-1,3,2',6'-tetrazidoneamine | 182554-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5,6,3',4'-tetra-O-acetyl-1,3,2',6'-tetrazidoneamine
• 英文别名: [(1S,2S,3R,4S,6R)-2-acetyloxy-4,6-diazido-3-[(2R,3R,4R,5R,6R)-4,5-diacetyloxy-3-azido-6-(azidomethyl)oxan-2-yl]oxycyclohexyl] acetate
• CAS: 182554-06-9
• 化学式: C₂₀H₂₆N₁₂O₁₀
• 分子量: 594.501
• InChiKey: ZUCZZVDZKZGYAP-QTZWXDKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  181
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  5,6,3',4'-tetra-O-acetyl-1,3,2',6'-tetrazidoneamine 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 3',4',5,6-tetra-O-acetyl-1-N-[(S)-2-O-benzyl-4-(benzyloxycarbonylamino)butanoyl]-3,2',6'-triazidoneamine
  参考文献：
  名称：

  Investigation of the Regioselectivity for the Staudinger Reaction and Its Application for the Synthesis of Aminoglycosides with N-1 Modification

  摘要：

  The criteria for controlling the regioselectivity of Staudinger reduction of azides have been investigated. These findings enable a convenient direct N-1 modification of the perazidoneamine and perazidoribostamycin resulting in the synthesis of aminoglycoside antibiotics with activity against drug-resistant bacteria.

  DOI：

  10.1021/jo062588j
• 作为产物：
  描述：

  neamine tetrahydrochloride 在 4-二甲氨基吡啶 、 triflyl azide 、 copper(II) sulfate 、 三乙胺 作用下， 以 吡啶 为溶剂， 生成 5,6,3',4'-tetra-O-acetyl-1,3,2',6'-tetrazidoneamine
  参考文献：
  名称：

  一种高效，改进的叠氮化三氟噻吩的制备方法及其在催化重氮转移反应中的应用

  摘要：

  描述了一种有效的和改进的制备三氟叠氮化物的方法，并将其应用于催化重氮转移反应。与以前的方案相比，剧毒的NaN 3和Tf 2 O试剂的量大大减少了。

  DOI：

  10.1016/j.tetlet.2005.10.103

文献信息

• Metal catalyzed diazo transfer for the synthesis of azides from amines
  作者：Phil B Alper、Shang-Cheng Hung、Chi-Huey Wong

  DOI：10.1016/0040-4039(96)01307-x

  日期：1996.8

  An improved method for the synthesis of azides is described. Diazo transfer from trifly azide effectively with Cu++, Ni++ or Zn++ as a catalyst. The process is amenable to scaleup, can be carried out using commercially available reagents and does not require anhydrous conditions. When metals are scavenged from the reaction, the rate drops by many orders of magnitude.

  描述了一种合成叠氮化物的改进方法。以Cu ++，Ni ++或Zn ++为催化剂，有效地从三fly叠氮化物中转移重氮。该方法适合扩大规模，可以使用可商购的试剂进行并且不需要无水条件。当从反应中清除金属时，速率下降许多数量级。
• Synthesis and antibacterial activity of novel neamine derivatives: preponderant role of the substituent position on the neamine core
  作者：Nicolas Gernigon、Valérie Bordeau、Fabienne Berrée、Brice Felden、Bertrand Carboni

  DOI：10.1039/c2ob07065k

  日期：——

  A series of neamine derivatives were prepared from the cyclic carbonate and sulfate of 1,3,2′,6′-tetraazido-3′,4′,-di-O-acetylneamine. Ring opening reactions with diversely substituted amines result in the formation of the corresponding carbamates or sulfonic acids with good overall yields. The antibacterial activities of the synthesized products against E. coli (DH5α) and S. aureus (RN4220) were evaluated

  由1,3,2'，6'-四叠氮基-3'，4'，-二-O-乙酰基亚胺的环状碳酸酯和硫酸酯制备了一系列的神经胺衍生物。与不同取代的胺的开环反应导致形成具有良好总收率的相应氨基甲酸酯或磺酸。评价了合成产物对大肠杆菌（DH5α）和金黄色葡萄球菌（RN4220）的抗菌活性。使用分离的单一区域异构体，证实了氨基甲酸酯取代基的5位在神经胺核心上的优越作用。
• An Efficient and General Route to the Synthesis of Novel Aminoglycosides for RNA Binding
  作者：Julia Revuelta、Andrés Santana、Ágatha Bastida、Teresa del Campo、Juan Asensio

  DOI：10.1055/s-0030-1259305

  日期：2011.1

  An alternative and straightforward method to prepare aminoglycoside dimers and heterodimeric conjugates is reported. The novel type of modification may provide a promising way for the development of new ligands effectively targeting to RNA.

  本报告介绍了制备氨基糖苷二聚体和异二聚体共轭物的另一种简单易行的方法。这种新型的修饰方法可能为开发有效靶向 RNA 的新配体提供了一种可行的途径。
• A Short and Scalable Route to Orthogonally <i>O</i>-Protected 2-Deoxystreptamine
  作者：Sebastiaan (Bas) A. M. W. van den Broek、Bas W. T. Gruijters、Floris P. J. T. Rutjes、Floris L. van Delft、Richard H. Blaauw

  DOI：10.1021/jo062369y

  日期：2007.4.1

  A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hydrolysis and two regioselective protective group manipulations involving acetylation and deacetylation. The synthetic route is amenable to scale-up for the production of multigram quantities of enantiopure and orthogonally O-protected 2-deoxystreptamine, a versatile scaffold for the generation of libraries of RNA-targeting ligands.
• Reexamination of Neomycin B Degradation:  Efficient Preparation of Its CD and D Rings as Protected Glycosyl Donors
  作者：Baogen Wu、Jun Yang、Yun He、Eric E. Swayze

  DOI：10.1021/ol026548n

  日期：2002.10.1

  [GRAPHICS]The degradation of neomycin B was reexamined, and a novel protocol was established to prepare the properly masked neomycin CD ring as a glycol donor in excellent yield. Glycosylation of the CD ring with glycol acceptors provided a facile access to versatile intermediates that could be utilized to synthesize a variety of novel neomycin B mimetics for RNA recognition.