2-Deoxy-2-formamido-D-glucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Deoxy-2-formamido-D-glucose
• 英文别名: 2-deoxy-2-formamido-D-glucopyranose；N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]formamide
• 化学式: C₇H₁₃NO₆
• 分子量: 207.183
• InChiKey: FVMMQJUBNMOPPR-YDEIVXIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Deoxy-2-formamido-D-glucose 在 偶氮二异丁腈 、 三正丁基氢锡 、 三乙胺 、 三氯氧磷 作用下， 以 吡啶 、 二氯甲烷 、 甲苯 为溶剂， 反应 14.0h， 生成 1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-arabinohexopyranose
  参考文献：
  名称：

  与氨基糖苷类抗生素化学反应有关的反应。第14部分。有用的自由基脱氨反应

  摘要：

  使用三正丁基锡烷在自由基条件下将伯，仲和叔脂族或脂环族异氰酸酯平稳还原为相应的烃。减少的相对难度是三级>二级>一级。在这些条件下不还原芳族异氰化物。通过三正丁基锡烷还原异硫氰酸酯（或异戊烯异氰酸酯）也可提供烃，但此处异氰酸酯已被证明是中间体。在1，2-关系中具有异氰酸酯和黄原酸酯官能团的化合物的还原产生平滑的自由基断裂，从而提供烯烃。描述了从葡糖胺开始的2-脱氧-D-葡萄糖的有效合成。

  DOI：

  10.1039/p19800002657
• 作为产物：
  描述：

  甲酸 、 D-氨基葡萄糖盐酸盐 生成 2-Deoxy-2-formamido-D-glucose
  参考文献：
  名称：

  Synthesis of some p-nitrophenyl 2-acylamino-2-deoxy-d-glucosides and their hydrolysis with the β-d-hexosaminidase from Hohenbuehelia serotina

  摘要：

  DOI：

  10.1016/s0008-6215(00)83565-x

文献信息

• Hydrolytic and transglycosylation reactions of N-acyl modified substrates catalysed by β-N-acetylhexosaminidases
  作者：Pavla Fialová、Lenka Weignerová、Jana Rauvolfová、Věra Přikrylová、Andrea Pišvejcová、Rüdiger Ettrich、Marek Kuzma、Petr Sedmera、Vladimı́r Křen

  DOI：10.1016/j.tet.2003.10.111

  日期：2004.1

  hydrolytic and transglycosylation capabilities of 35 fungal β-N-acetylhexosaminidases with p-nitrophenyl 2-amino-2-deoxy-β-d-glucopyranoside and its four N-acyl derivatives (CHO, COCH2OH, COCH2CH3, COCF3) as substrates were tested. The preparation of four novel p-nitrophenyl disaccharides from these unnatural substrates catalysed by enzymes from Aspergillus oryzae, Penicillium oxalicum and Talaromyces flavus

  35种真菌β- N-乙酰基己糖胺酶与对硝基苯基2-氨基-2-脱氧-β-d-吡喃葡萄糖苷及其4种N-酰基衍生物（CHO，COCH 2 OH，COCH 2 CH 3的水解和转糖基化能力），COCF 3）作为底物进行了测试。的四种新型制备p硝基苯基二糖从由酶催化的这些非天然底物的米曲霉，草酸青霉和踝节菌属菌代表了相当大的扩展糖苷酶的合成潜力。
• Isonitriles as Alkyl Radical Precursors in Visible Light Mediated Hydro‐ and Deuterodeamination Reactions**
  作者：Irene Quirós、María Martín、Miguel Gomez‐Mendoza、María Jesús Cabrera‐Afonso、Marta Liras、Israel Fernández、Luis Nóvoa、Mariola Tortosa

  DOI：10.1002/anie.202317683

  日期：2024.2.12

  We report the use of isonitriles as alkyl radical precursors in visible-light mediated hydro- and deuterodeamination reactions. Most examples only require visible-light irradiation of the isonitrile in the presence of a silyl radical precursor, although a significant acceleration was observed in the presence of an organic photocatalyst. The method is scalable, shows broad functional group compatibility

  我们报道了在可见光介导的加氢和氘代脱氨基反应中使用异腈作为烷基自由基前体。大多数例子仅需要在甲硅烷基自由基前体存在下对异腈进行可见光照射，尽管在有机光催化剂存在下观察到显着的加速。该方法具有可扩展性，显示出广泛的官能团兼容性，并且适用于 C α伯、C α仲和 C α叔烷基异腈。
• Phosphorylase-catalyzed N-formyl-α-glucosaminylation of maltooligosaccharides
  作者：Satoshi Kawazoe、Hironori Izawa、Mutsuki Nawaji、Yoshiro Kaneko、Jun-ichi Kadokawa

  DOI：10.1016/j.carres.2010.01.001

  日期：2010.3

  This paper describes the phosphorylase-catalyzed enzymatic N-formyl-alpha-glucosaminylation of maltooligosaccharides for direct incorporation of 2-deoxy-2-formamido-alpha-D-glucopyranose units into maltooligosaccharides. When the reaction of 2-deoxy-2-formamido-alpha-D-glucopyranose-1-phosphate (GlcNF-1-P) as the glycosyl donor and maltotetraose as a glycosyl acceptor was performed in the presence of phosphorylase, the N-formyl-alpha-D-glucosaminylated pentasaccharide was produced, as confirmed by MALDI-TOF MS. Furthermore, the glucoamylase-catalyzed reaction of the crude products supported that the 2-deoxy-2-formamido-alpha-D-glucopyranoside unit was positioned at the non-reducing end of the pentasaccharide. The pentasaccharide was isolated from the crude products and its structure was further determined by the (1)H NMR analysis. On the other hand, when the phosphorylase-catalyzed reactions of maltotriose and maltopentaose using GlcNF-1-P were conducted, no N-formyl-alpha-glucosaminylation took place in the former system, whereas the latter system gave N-formyl-alpha-D-glucosaminylated oligosaccharides with various degrees of polymerization. These results could be explained by the recognition behavior of phosphorylase toward maltooligosaccharides. (C) 2010 Elsevier Ltd. All rights reserved.
• Lipid Analogs of the Nodulation Factors Using the Ugi/Passerini Multicomponent Reactions: Preliminary Studies on the Carbohydrate Monomer
  作者：Jean-Marie Beau、Nathalie Grenouillat、Boris Vauzeilles

  DOI：10.3987/com-07-s(u)60

  日期：——