Oxidation of aldose oximes. Formation and structure of hydroxydiazene oxide acetals and preparation of hydroximolactones. X-Ray crystal structure of 2,3:5,6-di-O-isopropylidene-α-<scp>D</scp>-mannofuranosyl-ONN-azoxy 2,3:5,6-di-O-isopropylidene-α-<scp>D</scp>-mannofuranoside

Aebischer, Bernard; Hanssen, Harald W.; Vasella, Andrea; Schweizer, W. Bernd

doi:10.1039/p19820002139

Cited by 53 publications

(30 citation statements)

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“…The relative intensities of the two bands depend on the structure of the hydroximo-lactones and the solvent. The IR spectrum of 9 in KBr shows only one C=N band.The furanoid hydroximo lactone 11 has only one C=N absorption [14]. The characteristic data of these glycosylidene-derived diaziridines are listed in Table 1.…”

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Glycosylidene Carbenes a new approach to glycoside synthesis. Part 1. Preparation of glycosylidene‐derived diaziridines and diazirines

Briner

Vasella

1989

Helvetica Chimica Acta

105

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“…Preparation of (Glycosy1idene)amino Sulfonates (see Scheme 3). The preparation of the aldonhydroximo-lactones 9, 10, and 11 has already been described [14] [ 151. Similarly, the galactonhydroximo-lactone 13 was prepared by oxidation of the crystalline aldoxime 12 with MnO, in MeOH [15] in a yield of 75%.…”

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Glycosylidene Carbenes a new approach to glycoside synthesis. Part 1. Preparation of glycosylidene‐derived diaziridines and diazirines

Briner

Vasella

1989

Helvetica Chimica Acta

105

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“…[10,31,32] Before that, Vasella et al had synthesized the glycosides 8 and 9 by oxidation of diisopropylidenemannose oxime or tetra-O-benzylglucosylamine, respectively. [33] The structure of compound 8 was confirmed by X-ray analysis.…”

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confidence: 62%

“…[10,33,[43][44][45][46][47][48] The salt 13 proved to be quite stable: unlike other 2-substituted diazene-1-olates-2-oxides, which are known to eliminate NO or N 2 O, compound 13 can be stored at room temperature over months without decomposition. The 1 H NMR spectrum of a solution of 13 in D 2 O remained unchanged after the sample had been boiled for three minutes.…”

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Nitrosation of Sugar Oximes: Preparation of 2‐Glycosyl‐1‐hydroxydiazene‐2‐oxides

Brand¹,

Huhn²,

Groth³

et al. 2005

Chemistry A European J

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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‐(β‐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‐(β‐d‐mannopyranosyl)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‐(α‐D‐mannofuranosyl)‐1‐hydroxydiazene‐2‐oxide salts 34 and 35, respectively. Methylation of the ammonium 2‐(β‐D‐glucopyranosyl)‐1‐hydroxydiazene‐2‐oxide 13 yielded the 1‐methoxy compound, which was benzoylated to afford the tetra‐O‐benzoate 14 a, 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‐acetyl‐β‐D‐glucopyranosylamine 18 was prepared. The structure of this compound was confirmed by X‐ray diffraction analysis. Treatment of acetobromoglucose with cupferron furnished the 1‐(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyloxy)‐2‐phenyldiazene‐2‐oxide 20.

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“…Under similar conditions, but in the presence of 2.5 equiv. of NaPO(OMe), the chloronitromannofuranose 10 gave the hydroximo-lactone 11 (21 %) [26], the nitrile 12 (lo%), the nitromannofuranose 13 (12%) [27], and starting material 10 (36%). No trace of a (1-C-nitroglycosy1)phosphonate was found.…”

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Deoxy‐nitrosugars. 11^th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer

Meuwly

Vasella

1985

Helvetica Chimica Acta

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Treatment of the chloro-nitro-ribofuranose 7 with KPO(OMe)2 gave the 0-amino phosphate 8 (5%) and the nitrile 9 (62%). Compound 9 was also obtained by the reaction of 8 with KPO(OMe),, and its structure was established by X-ray analysis. Treatment of the chloro-nitro-mannofuranose 10, the bromo-nitro-ribofuranose 14, or the bromo-nitro-mannofuranose 16, respectively, with the K or Na salt of HPO(OMe)2 lead also to 0-amino phosphates and nitriles. The (1-C-nitrog1ycosyl)phosphonate 22 was obtained (21 %) together with the nitrile 21 (5 1 %) from the chloro-nitro-mannofuranose 10 and KPO(OEt)2. The reaction of the I-C-nitroglycosyl sulfone 25 (NO2-group endo) with KPO(OEt), gave the (I-C-nitroglycosy1)phosphonate 22 (61 %) and the nitrile 21 (1 1 YO), whilst the anomeric sulfone 26 (NO,-group exo) gave 22 (15%) and 21 (58%). In the presence of [18]crown-6, a mixture of the anomers 25 and 26 gave the (I-C-nitroglycosy1)phosphonate 22 in 67% yield together with 21 (13%). These findings are rationalized as the result of a competition between a nucleophilic attack of the dialkyl-phosphite anions on the NO2-group leading ultimately to the nitrile 21 and a single-electron transfer reaction leading to the (1-C-nitroglycosy1)phosphonate 22.

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Oxidation of aldose oximes. Formation and structure of hydroxydiazene oxide acetals and preparation of hydroximolactones. X-Ray crystal structure of 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl-ONN-azoxy 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside

Abstract: Oxidation des Glucopyranosylamins (II) liefert je nach Lösungsmittel die Verbindung (I) bzw. das Dimer (III).

Cited by 53 publications

References 1 publication

Glycosylidene Carbenes a new approach to glycoside synthesis. Part 1. Preparation of glycosylidene‐derived diaziridines and diazirines

Glycosylidene Carbenes a new approach to glycoside synthesis. Part 1. Preparation of glycosylidene‐derived diaziridines and diazirines

Nitrosation of Sugar Oximes: Preparation of 2‐Glycosyl‐1‐hydroxydiazene‐2‐oxides

Deoxy‐nitrosugars. 11^th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer

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Oxidation of aldose oximes. Formation and structure of hydroxydiazene oxide acetals and preparation of hydroximolactones. X-Ray crystal structure of 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl-ONN-azoxy 2,3:5,6-di-O-isopropylidene-α-D-mannofuranoside

Abstract: Oxidation des Glucopyranosylamins (II) liefert je nach Lösungsmittel die Verbindung (I) bzw. das Dimer (III).

Cited by 53 publications

References 1 publication

Glycosylidene Carbenes a new approach to glycoside synthesis. Part 1. Preparation of glycosylidene‐derived diaziridines and diazirines

Glycosylidene Carbenes a new approach to glycoside synthesis. Part 1. Preparation of glycosylidene‐derived diaziridines and diazirines

Nitrosation of Sugar Oximes: Preparation of 2‐Glycosyl‐1‐hydroxydiazene‐2‐oxides

Deoxy‐nitrosugars. 11th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer

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Deoxy‐nitrosugars. 11^th Communication. Reactions of 1‐C‐nitroglycosyl halides and 1‐C‐nitroglycosyl sulfones with dialkyl‐phosphite anions: Nucleophilic attack vs. single‐electron transfer