81846-60-8

Basic information

• Product Name: BETA-D-GLUCOPYRANOSYL NITROMETHANE
• Synonyms: BETA-D-GLUCOPYRANOSYL NITROMETHANE;b-D-Glucopyranosylnitromethane;SS-D-GLUCOPYRANOSYL NITROMETHANE;nitroMethyl β-D-glucopyranoside
• CAS NO: 81846-60-8
• Molecular Formula: C₇H₁₃NO₇
• Molecular Weight: 223.18062
• Mol File: 81846-60-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174-175 °C
• Boiling Point: 497.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.584±0.06 g/cm3(Predicted)
• PKA: 7.18±0.70(Predicted)
• CAS DataBase Reference: BETA-D-GLUCOPYRANOSYL NITROMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-D-GLUCOPYRANOSYL NITROMETHANE(81846-60-8)
• EPA Substance Registry System: BETA-D-GLUCOPYRANOSYL NITROMETHANE(81846-60-8)

Safety Data

• Hazardous Substances Data: 81846-60-8(Hazardous Substances Data)

Upstream product

• 25541-53-1 1-Desoxy-1-nitro-D-glycero-D-gulo-heptitol 
• 2280-44-6 D-Glucose 
• 75-52-5 nitromethane 
• 50-99-7 D-glucose 
• 492-61-5 β-D-glucose 
• 14199-89-4 1?deoxy?1?nitro?D?glycero?D?galacto?heptitol 
• 16749-54-5 1,2?dideoxy?1?nitro?D?manno?hept?1?enitol peracetate 

Downstream Products

• 136738-66-4 2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol 
• 136738-59-5 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol 
• 169597-64-2 (2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid 
• 156058-64-9 (2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Nitroalkene ring closure route to carbon-linked scaffolds for mimicking α-d-mannopyranosyl natural linkage

Abstract: Controlled treatment of 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-d-manno-hept-1-enitol with sodium methoxide in methanol was stopped by decationization at a point providing about equimolar mixture of α-d-mannopyranosyl and β-d-mannopyranosyl nitromethanes, from which the target α-anomer was isolated by chemisorption chromatography on a cation exchange resin in the Ba2+ form in a 36% yield. Direct reduction of the above mixture with ferrous hydroxide in situ to the corresponding amines, followed by the selective N-acetylation and the analogical chromatographic separation of both pertinent isomers with their stable ring structures gave N-acetyl-C-α-d-mannopyranosyl-methylamine. Alternative stopping of the initial ring forming reaction with acidified methanol at the above given product ratio initiated a subsequent Nef reaction and α-d-mannopyranosyl methanal dimethyl acetal was then chromatographically separated from its β-isomer on an anion exchange resin in the OH? form. Activations of two latter C-α-d-mannopyranosyl scaffolds by acid hydrolysis into respective reactive free amine or aldehyde forms were developed as well. Detailed reinvestigation of the classical method of preparation of d-mannosyl nitromethanes by thermal dehydration of a 1-deoxy-1-nitroalditol derived from d-mannose showed a maximum occurrence of only 18% of the required α-d-mannopyranosyl anomer. Graphic abstract: [Figure not available: see fulltext.].

3,4-Dipyranosyl-1,2,5-oxadiazole 2-oxides: Synthesis and X-ray structure

3,4-Di(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-1,2,5-oxadiazole 2-oxide (7) has been synthesised from D-mannose by a route involving as the key step dimerisation of mannopyranosyl nitrile oxide 2. Three methods were used for the generation of the nitrile oxide: isocyanate-mediated dehydration of nitromethylmannose derivative 4, treatment of aldoxime 5 with aq. hypochlorite, and base-induced dehydrochlorination of hydroximoyl chloride 6. D-Gluco, D-galacto, D-xylo, and L-fucopyranosyl analogues 8-11 were prepared similarly. The structure of D-mannose-derived 1,2,5-oxadiazole 2-oxide 7 was established by X-ray crystallography.

Eine Zuckeraminosaeure als neuartiges Peptidmimetikum

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