3-deoxy-β-D-glucose | 75800-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-β-D-glucose
• 英文别名: 3-deoxy-D-ribo-hexose；β-D-ribo-3-deoxy-hexopyranose；β-D-ribo-3-Desoxy-hexopyranose；3-Deoxy-Beta-D-Ribo-Hexopyranose；(2R,3R,5S,6R)-6-(hydroxymethyl)oxane-2,3,5-triol
• CAS: 75800-77-0
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: RJDIFQMDPPUATQ-SLPGGIOYSA-N

物化性质

• 熔点：
  137 °C(Solv: ethanol, 95% (64-17-5))
• 沸点：
  396.9±42.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-deoxy-β-D-glucose 在 吡啶 、 sodium hydroxide 、 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.42h， 生成 9-(2',3'-Dideoxy-6'-O-<(4,4'-dimethoxytriphenyl)methyl>-β-D-glucopyranosyl)-N²-isobutyrylguanin
  参考文献：
  名称：

  Warum Pentose- and nichtHexose-Nucleinsäuren??。泰尔二世。寡核苷酸aus 2'，3'-Dideoxy-β-D-glucopyranosyl-Bausteinen（'Homo-DNS'）：Herstellung。†

  摘要：

  为什么是戊糖而不是己糖核酸？第二部分。包含2'，3'-双脱氧-β-D-吡喃葡萄糖基结构单元的寡核苷酸的制备（7）

  DOI：

  10.1002/hlca.19920750503
• 作为产物：
  描述：

  3-deoxy-D-ribo-hexopyranose 以 水 为溶剂， 生成 3-deoxy-β-D-glucose
  参考文献：
  名称：

  3-Deoxy-β-D-ribo-hexopyranose (3-deoxy-β-D-glucopyranose)

  摘要：

  The beta- pyranose form, ( III), of 3- deoxy- D- ribo- hexose ( 3- deoxy- D- glucose), C6H12O5, crystallizes from water at 298 K in a slightly distorted C-4(1) chair conformation. Structural analyses of ( III), beta- D- glucopyranose, ( IV), and 2- deoxy- beta- D-arabinohexopyranose ( 2- deoxy- beta- D- glucopyranose), ( V), show significantly different C - O bond torsions involving the anomeric carbon, with the H - C - O - H torsion angle approaching an eclipsed conformation in ( III) (. 10.9 degrees) compared with 32.8 and 32.5 degrees in ( IV) and ( V), respectively. Ring carbon deoxygenation significantly affects the endo- and exocyclic C - C and C - O bond lengths throughout the pyranose ring, with longer bonds generally observed in the monodeoxygenated species ( III) and ( V) compared with ( IV). These structural changes are attributed to differences in exocyclic C - O bond conformations and/ or hydrogenbonding patterns superimposed on the direct ( intrinsic) effect of monodeoxygenation. The exocyclic hydroxymethyl conformation in ( III) ( gt) differs from that observed in ( IV) and ( V) ( gg).

  DOI：

  10.1107/s0108270107038553

文献信息

• Synthesis of 1,5-Anhydro- d -fructose derivatives and evaluation of their inflammasome inhibitors
  作者：Kohtaro Goto、Hiroko Ideo、Akiko Tsuchida、Yuriko Hirose、Ikuro Maruyama、Satoshi Noma、Takashi Shirai、Junko Amano、Mamoru Mizuno、Akio Matsuda

  DOI：10.1016/j.bmc.2017.11.041

  日期：2018.7

  Synthesis of several 1,5-Anhydro-d-fructose (1,5-AF) derivatives to evaluate inhibitory activities of the inflammasome was carried out. Recently, 1,5-AF reported to suppress the inflammasome, although with only low activity. We focused on the hydration of 2-keto form of 1,5-AF and speculated that this hydration was the cause of low activity. Therefore, we synthesized some 1,5-AF derivatives that would

  几个1,5-脱水-的合成d -fructose（1,5- AF）衍生物的炎性进行评价抑制活性。近来，据报道1，5-AF抑制炎症小体，尽管活性低。我们着眼于2-酮形式的1,5-AF的水合，并推测这种水合是低活性的原因。因此，我们合成了一些1,5-AF衍生物，这些衍生物将无法形成二聚体构象，并且有望对炎症小体具有较高的活性，然后通过使用小鼠骨髓-核糖核酸评估它们对NLRP3炎症小体的抑制活性。衍生的巨噬细胞和人类THP-1细胞。结果，某些合成的2-酮形式的化合物对NLRP3炎性小体的抑制活性比1,5-AF高得多。
• Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against<i>Bacillus anthracis</i>
  作者：Catarina Dias、Alice Martins、Ana Pelerito、Maria C. Oliveira、Marialessandra Contino、Nicola A. Colabufo、Amélia P. Rauter

  DOI：10.1002/ejoc.201801764

  日期：2019.3.31

  against antibiotic resistance emergence relies on the development of alternative antibiotics. Approaches towards new dodecyl deoxy and dideoxy glycosides were devised and compounds tested over Bacillus spp. and Enterococcus faecalis. The 4,6‐dideoxygenation pattern gave the most active glycoside against all tested microbes.

  对抗抗生素耐药性的出现有赖于替代抗生素的开发。设计了新的十二烷基脱氧和双脱氧糖苷的方法，并通过芽孢杆菌（Bacillus spp）对化合物进行了测试。和粪肠球菌。4,6-去氧合模式对所有受试微生物的糖苷活性最高。
• [EN] β-1,6-GLUCAN THERAPEUTIC ANTIBODY CONJUGATES<br/>[FR] CONJUGUÉS D'ANTICORPS THÉRAPEUTIQUE DE β-1,6-GLUCANE
  申请人：INNATE BIOTHERAPEUTICS LLC

  公开号：WO2018106645A1

  公开（公告）日：2018-06-14

  The present invention encompasses embodiments in which a therapeutic antibody is conjugated to β-1,6-glucan oligomers. Thus, the present invention includes, among other things, compositions including a therapeutic antibody conjugated to one or more β-1-,6-glucan oligomers. The present invention further includes, among other things, methods of making and/or using such β-1,6-glucan conjugates. In certain embodiments, a β-1,6-glucan conjugate of the present invention is useful as a therapeutic or in a method of therapy.

  本发明涵盖了将治疗性抗体与β-1,6-葡聚糖寡聚体结合的实施方式。因此，本发明包括包含治疗性抗体与一个或多个β-1,6-葡聚糖寡聚体结合的组合物，以及制备和/或使用这种β-1,6-葡聚糖结合物的方法。在某些实施方式中，本发明的β-1,6-葡聚糖结合物可用作治疗性药物或治疗方法。
• 3-Désoxy oligosaccharides, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：SANOFI

  公开号：EP0621282B1

  公开（公告）日：1997-07-09
• PHARMACEUTICAL FORMULATIONS EMPLOYING SHORT-CHAIN SPHINGOLIPIDS AND THEIR USE
  申请人：HET NEDERLANDS KANKER INSTITUUT (The Netherlands Cancer Institute)

  公开号：EP1686959B1

  公开（公告）日：2009-06-24