1-Desoxy-N-hydroxy-β-D-glucopyranosylamin | 57820-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Desoxy-N-hydroxy-β-D-glucopyranosylamin
• 英文别名: N-β-D-[glucopyranosyl]-hydroxylamine；N-β-D-glucopyranosylhydroxylamine；N-hydroxy-β-D-glucopyranosylamine；D-glucose oxime；Glucopyranosylhydroxylamin；(2R,3R,4S,5S,6R)-2-(hydroxyamino)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 57820-45-8
• 化学式: C₆H₁₃NO₆
• 分子量: 195.172
• InChiKey: KXJMZHQGEGAKAK-VFUOTHLCSA-N

物化性质

• 熔点：
  120-122 °C (decomp)
• 沸点：
  500.0±55.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.23
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  122.41
• 氢给体数：
  6.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-Desoxy-N-hydroxy-β-D-glucopyranosylamin 在 对甲苯磺酸 臭氧 、 sodium hydrogensulfite 、 zinc(II) chloride 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 1-deoxy-1-nitro-4,6-O-benzylidene-β-D-glucose
  参考文献：
  名称：

  脱氧硝基唑。13. Mitteilung。HerstellungUngeschützterand PartiellGeschützter1-Desoxy-1-nitro-D-aldosen sowieRöntgenstrukturanalyseneiniger ihrer Vertreter †

  摘要：

  未保护和部分保护的1-脱氧-1-硝基-D-醛糖的制备及一些代表性的X射线结构分析

  DOI：

  10.1002/hlca.19860690526
• 作为产物：
  描述：

  可得然胶 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 1-Desoxy-N-hydroxy-β-D-glucopyranosylamin
  参考文献：
  名称：

  Preparation and stereoselectivity of 1,3-dipolar cycloaddition ofD-glucose-derived nitrones to N-arylmaleimides

  摘要：

  Nitrones 2 derived from D-glucose oxime and benzaldehydes without employing any protection of hydroxyl group were isolated in pure state. The 1,3-dipolar cycloaddition of 2 to N-arylmaleimides gave predominantly the anti isoxazolidines 3 and was rationalized by Z/E isomerization of N-glycosylnitrones 2. The structure and steric configuration of the products have been assigned on the basis of H-1- and C-13-NMR spectroscopy. AM1 calculations of the nitrones and MM2 calculations of the adducts were performed.

  DOI：

  10.1007/bf00814148

文献信息

• Nitrosation of Sugar Oximes: Preparation of 2-Glycosyl-1-hydroxydiazene-2-oxides
  作者：Jörg Brand、Thomas Huhn、Ulrich Groth、Johannes C. Jochims

  DOI：10.1002/chem.200500325

  日期：2006.1

  Oximes of glucose, xylose, lactose, fructose, and mannose have been prepared. Nitrosation of the oximes of glucose, xylose, and lactose with NaNO2/HCl afforded 2-(beta-glycopyranosyl)-1-hydroxydiazene-2-oxides, which were isolated as salts 13, 22, and 28. Nitrosation of fructose oxime 29 furnished fructose, whereas nitrosation of mannose oxime 30 with NaNO2/HCl afforded the 1-hydroxy-2-(beta-D-man

  已经制备了葡萄糖，木糖，乳糖，果糖和甘露糖的肟。用NaNO 2 / HCl亚硝化葡萄糖，木糖和乳糖的肟，得到2-（β-甘露糖基）-1-羟基二氮杂-2-氧化物，其被分离为盐13、22和28。提供了果糖肟的亚硝化29果糖，而甘露糖肟30用NaNO2 / HCl的亚硝化得到1-羟基-2-（β-D-甘露吡喃糖基）二氮杂-2-氧化物32，由此制得对茴香醚鎓盐31和钠盐33。然而，在CsOH或KOH的水溶液中用亚硝酸异戊酯亚硝化30，导致分别形成2-（α-D-甘露呋喃糖基）-1-羟基二氮杂2-氧化物盐34和35。2-（β-D-吡喃葡萄糖基）-1-羟基二氮杂-2-氧化物铵13的甲基化产生1-甲氧基化合物，将其苯甲酰化得到四-O-苯甲酸酯14a，通过X射线衍射分析证实其结构。由葡萄糖O-甲基肟15和16制备N-甲氧基-N-亚硝基-2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖胺18。该化合物的结构通过
• Synthesis and photosensitivity of isoxazolin-5-one glycosides
  作者：Tobias Becker、Prashant Kartikeya、Christian Paetz、Stephan H. von Reuß、Wilhelm Boland

  DOI：10.1039/c5ob00244c

  日期：——

  A novel procedure for the synthesis of isoxazolin-5-one glycosides starting from unprotected carbohydrates is described. The substrate scope of the one-pot synthetic protocol was explored using D-configured glucose, xylose, maltose, fructose, ribose and 2-deoxyribose. Naturally occurring 2-(β-D-glucopyranosyl)-3-isoxazolin-5-one and four novel isoxazolin-5-one glycosides derived from xylose, maltose

  描述了一种从未保护的碳水化合物开始合成异恶唑啉-5-酮糖苷的新方法。使用D-构型的葡萄糖，木糖，麦芽糖，果糖，核糖和2-脱氧核糖探索一锅合成方案的底物范围。合成了天然存在的2-（β- D-吡喃葡萄糖基）-3-异恶唑啉-5-酮和四种衍生自木糖，麦芽糖和果糖的新型异恶唑啉-5-酮糖苷，并通过快速色谱法纯化。根据化学结构，光物理性质以及pH稳定性对化合物进行了表征。将合成的糖苷的光水解速率与尿苷作为标准进行比较，以确定水中光反应的量子产率。
• Chemoselective coupling of sugar oximes and α-ketoacids to glycosyl amides and N-glycopeptides
  作者：Claudia Pöhner、Vera Ullmann、Ramona Hilpert、Eric Samain、Carlo Unverzagt

  DOI：10.1016/j.tetlet.2014.02.056

  日期：2014.4

  The reaction of unprotected sugar hydroxylamines and oximes with α-ketoacids leads to the chemoselective formation of glycosyl amides following the decarboxylative condensation pathway of Bode’s ketoacid hydroxylamine (KAHA) ligation. Sugar oximes with gluco configuration stereoselectively form β-linked products. This method can be used for the convergent synthesis of N-acylated sugars and oligosaccharides

  未保护的糖羟胺和肟与α-酮酸的反应会导致Bode酮酸羟胺（KAHA）的脱羧缩合路径发生化学选择性的糖基酰胺形成。具有葡萄糖构型的糖肟立体选择性地形成β-连接的产物。该方法可用于收敛合成在酰基部分带有小标记，间隔基或肽的N-酰化糖和寡糖。
• Hydrophosphorylation of monosaccharides oximes and hydrazones
  作者：A. A. Bobrikova、M. P. Koroteev、I. I. Levina、E. E. Nifant’ev

  DOI：10.1134/s1070363209080064

  日期：2009.8

  The hydrophosphorylation of monosaccharides oximes and hydrazones was studied; similarity and difference of this process compared to the reaction of secondary glycosylamines with the hydrophosphoryl compounds are shown. A number of the original alpha-aminophosphoryl compounds is obtained including those containing carbohydrate fragment in their compositions.
• Nagel, Yvonne; Beck, Wolfgang, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1986, vol. 41, # 11, p. 1447 - 1454
  作者：Nagel, Yvonne、Beck, Wolfgang

  DOI：——

  日期：——