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首页> 外文期刊>Chemistry: A European journal >Nitrosation of Sugar Oximes: Preparation of 2-Glycosyl-l-hydroxydiazene-2-oxides
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Nitrosation of Sugar Oximes: Preparation of 2-Glycosyl-l-hydroxydiazene-2-oxides

机译：糖肟的亚硝化：2-糖基-1-羟基二氮杂-2-氧化物的制备

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摘要

Oximes of glucose,xylose,lactose,fructose,and mannose have been prepared.Nitrosation of the oximes of glucose,xylose,and lactose with NaNO_2/HCl afforded 2-(beta-glyco-pyranosyl)-l-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 NaNO_2/HCl afforded the l-hydroxy-2-(beta-D-manno-pyranosyl)diazene-2-oxide 32,from which the p-anisidinium salt 31 and the sodium salt 33 were prepared.However,nitrosation of 30 with isopentyl nitrite in aqueous solutions of CsOH or KOH resulted in the formation of the 2-(alpha-D-mannofuranosyl)-l-hydroxydia-zene-2-oxide salts 34 and 35,respectively.Methylation of the ammonium 2-(beta-D-glucopyranosyl)-l-hydroxydia-zene-2-oxide 13 yielded the 1-methoxy compound,which was benzoylated to afford the tetra-O-benzoate 14a,the structure of which was confirmed by X-ray diffraction analysis.From the glucose O-methyloximes 15 and 16 the N-methoxy-N-nitroso-2,3,4,6-tetra-O-ace-tyl-beta-D-glucopyranosylamine 18 was prepared.The structure of this compound was confirmed by X-ray diffraction analysis.Treatment of acetobro-moglucose with cupferron furnished the l-(2,3,4,6-tetra-O-acetyl-beta-D-gluco-pyranosyloxy)-2-phenyldiazene-2-oxide 20.
机译：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，得到了2-（β-糖基-吡喃糖基）-1-羟基二氮杂-2-氧化物，分别以盐13,22和28的形式分离。果糖肟的亚硝化作用29提供了果糖，而甘露糖肟30与NaNO_2 / HCl的亚硝化作用得到了1-羟基-2-（β-D-甘露聚糖基）二氮杂-2氧化物32，制得对苯二甲铵盐31和钠盐33。然而，在CsOH或KOH水溶液中亚硝酸异戊酯亚硝化30导致2-（α-D-甘露呋喃糖基）的形成-l-羟基二茂氮-2-氧化物盐34和35.2-（β-D-吡喃吡喃糖基）-1-羟基二茂氮-2-氧化物13的甲基化反应生成1-甲氧基化合物，为苯甲酰化得到四-O-苯甲酸酯14a，其结构通过X射线衍射分析确定。从葡萄糖O-甲基肟15和16中，N-甲氧基-N-亚硝基制备了-2,3,4,6-四-O-乙酰基-β-D-吡喃葡萄糖基胺18，通过X射线衍射分析确定了该化合物的结构。 -（2,3,4,6-四-O-乙酰基-β-D-葡萄糖-吡喃葡糖氧基）-2-苯基二氮烯-2-氧化物20。

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