81812-47-7

Upstream product

• 16749-54-5 1,2?dideoxy?1?nitro?D?manno?hept?1?enitol peracetate 
• 14199-89-4 1?deoxy?1?nitro?D?glycero?D?galacto?heptitol 
• 35800-09-0 7-deoxy-7-nitro-L-glycero-L-galactoheptitol hexaacetate 
• 16749-54-5 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-D-galacto-hept-1-enitol 
• 1299346-94-3 C₇H₁₃NO₇ 

Relevant academic research and scientific papers

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.].

Preparation of D-galactofuranosyl nitromethanes: A revision and a new approach

Sodium methoxide-promoted methanolysis of 7-deoxy-7-nitro-l-glycero-l- galacto-heptitol peracetate rapidly and nearly quantitatively accumulates 7-deoxy-6-O-methyl-7-nitro-l-glycero-l-galacto-heptitol. The prolonged treatment then provides 76% of d-galactofuranosyl nitromethanes and finally results in the equilibrium of 77% of β-d-galactopyranosyl nitromethane and 7-9% of three other tautomeric d-galactosyl nitromethanes. Thermal treatment of 7-deoxy-7-nitro-l-glycero-l-galacto-heptitol in boiling water peaks at a 58% content of d-galactofuranosyl nitromethanes and ends in a similar equilibrium mixture of four d-galactosyl tautomers. The relevant kinetic parameters of the latter transformation are determined by a curve fitting using the nonlinear least-squares Marquardt-Levenberg algorithm.