2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-D-mannopyranose | 63597-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-D-mannopyranose
• 英文别名: [(2R,3S,4R,5S)-5-acetamido-4,6-diacetyloxy-2-(hydroxymethyl)oxan-3-yl] acetate
• CAS: 63597-75-1
• 化学式: C₁₄H₂₁NO₉
• 分子量: 347.322
• InChiKey: VMFNIHQAYQFWOI-DYPLGBCKSA-N

物化性质

• 沸点：
  524.5±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-D-mannopyranose 在 三氯化铁 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以70%的产率得到2-acetamido-3,4-di-O-acetyl-1,6-anhydro-2-deoxy-β-D-mannopyranose
  参考文献：
  名称：

  利用溶剂作用和催化量的路易斯酸轻松制备1,6-脱水己糖。

  摘要：

  在6位无保护并在端基中心带有O-甲基，S-乙基，O-乙酰基和OH-基团的单糖的回流溶液，在含有催化量路易斯酸（O.1-0.4当量。）以良好至高收率得到1,6-脱水己基吡喃糖。甲基2,3,4-三-O-二氘代苄基-α-D-糖苷（87-91％）获得了最佳结果。使用二异氘苄基保护基来促进NMR谱图的解释。

  DOI：

  10.3891/acta.chem.scand.48-0228
• 作为产物：
  描述：

  (7-acetamido-6-acetyloxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl) acetate 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 吡啶 、 水 、 溶剂黄146 为溶剂， 反应 98.5h， 生成 2-acetamido-1,3,4-tri-O-acetyl-2-deoxy-D-mannopyranose
  参考文献：
  名称：

  Fluorinated carbohydrates as potential plasma-membrane modifiers and inhibitors: synthesis of 2-amino-2,6-dideoxy-6-fluoro-D-mannopyranose hydrochloride

  摘要：

  DOI：

  10.1016/s0008-6215(00)85379-3

文献信息

• [EN] HYBRID SCFA-HYDROXYL-DERIVATIZED MONOSACCHARIDES, METHODS OF SYNTHESIS, AND METHODS OF TREATING DISORDERS<br/>[FR] MONOSACCHARIDES HYBRIDES DÉRIVATISÉS AVEC HYDROXYLE /SCFA (ACIDES GRAS À CHAÎNE COURTE), PROCÉDÉS DE SYNTHÈSE, ET PROCÉDÉS DE TRAITEMENT DE TROUBLES
  申请人：UNIV JOHNS HOPKINS

  公开号：WO2009020641A1

  公开（公告）日：2009-02-12

  Described herein are fatty acid carbohydrate-hydroxyl-hybrid compounds and derivatives thereof, and methods of treating or preventing disease and disease symptoms using the compounds and compositions thereof.

  本文描述了脂肪酸碳水化合物及其衍生物，以及利用这些化合物及其组合物治疗或预防疾病和疾病症状的方法。
• Hexosamine Template. A Platform for Modulating Gene Expression and for Sugar-Based Drug Discovery
  作者：Noha Elmouelhi、Udayanath Aich、Venkata D. P. Paruchuri、M. Adam Meledeo、Christopher T. Campbell、Jean J. Wang、Raja Srinivas、Hargun S. Khanna、Kevin J. Yarema

  DOI：10.1021/jm801661m

  日期：2009.4.23

  This study investigates the breadth of cellular responses engendered by short chain fatty acid (SCFA)-hexosamine hybrid molecules, a class of compounds long used in "metabolic glycoengineering" that are now emerging as drug candidates. First, a "mix and match" strategy showed that different SCFA (n-butyrate and acetate) appended to the same core sugar altered biological activity, complementing previous results [Campbell et al. J. Med. Chem. 2008, 51, 8135-8147] where a single type of SCFA elicited distinct responses. Microarray profiling then compared transcriptional responses engendered by regioisomerically modified ManNAc, GlcNAc, and GalNAc analogues in MDA-MB-231 cells. These data, which were validated by qRT-PCR or Western analysis for IDI, TP53, HPSE, NQO1, EGR1, and VEGFA, showed a two-pronged response where a core set of genes was coordinately regulated by all analogues while each analogue simultaneously uniquely regulated a larger number of genes. Finally, AutoDock modeling supported a mechanism where the analogues directly interact with elements of the NF-kappa B pathway. Together, these results establish the SCFA-hexosamine template as a versatile platform for modulating biological activity and developing new therapeutics.
• Targeting GNE Myopathy: A Dual Prodrug Approach for the Delivery of <i>N</i>-Acetylmannosamine 6-Phosphate
  作者：Chiara Morozzi、Jana Sedláková、Michaela Serpi、Marialuce Avigliano、Rosangela Carbajo、Lucia Sandoval、Yadira Valles-Ayoub、Patrick Crutcher、Stephen Thomas、Fabrizio Pertusati

  DOI：10.1021/acs.jmedchem.9b00833

  日期：2019.9.12

  ProTides comprise an important class of prodrugs currently marketed and developed as antiviral and anticancer therapies. The ProTide technology employs phosphate masking groups capable of providing more favorable druglike properties and an intracellular activation mechanism for enzyme-mediated release of a nucleoside monophosphate. Herein, we describe the application of phosphoramidate chemistry to 1,3,4-O-acetylated N-acetylmannosamine (Ac(3)ManNAc) to deliver ManNAc-6-phosphate (ManNAc-6-P), a critical intermediate in sialic acid biosynthesis. Sialic acid deficiency is a hallmark of GNE myopathy, a rare congenital disorder of glycosylation (CDG) caused by mutations in GNE that limit the production of ManNAc-6-P. Synthetic methods were developed to provide a library of Ac(3)ManNAc-6-phosphoramidates that were evaluated in a series of studies for their potential as a treatment for GNE myopathy. Prodrug 12b showed rapid activation in a carboxylesterase (CPY) enzymatic assay and favorable ADME properties, while also being more effective than ManNAc at increasing sialic acid levels in GNE-deficient cell lines. These results provide a potential platform to address substrate deficiencies in GNE myopathy and other CDGs.