81846-64-2

Basic information

• Product Name: BETA-D-GALACTOPYRANOSYL NITROMETHANE
• Synonyms: BETA-D-GALACTOPYRANOSYL NITROMETHANE;2,6-Anhydro-7-deoxy-7-nitro-L-glycero-L-galacto-heptitol
• CAS NO: 81846-64-2
• Molecular Formula: C₇H₁₃NO₇
• Molecular Weight: 223.18062
• Mol File: 81846-64-2.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BETA-D-GALACTOPYRANOSYL NITROMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-D-GALACTOPYRANOSYL NITROMETHANE(81846-64-2)
• EPA Substance Registry System: BETA-D-GALACTOPYRANOSYL NITROMETHANE(81846-64-2)

Safety Data

• Hazardous Substances Data: 81846-64-2(Hazardous Substances Data)

Upstream product

• 75-52-5 nitromethane 
• 59-23-4 D-Galactose 
• 10257-28-0 D-Galactose 
• 1299346-94-3 C₇H₁₃NO₇ 
• 16749-54-5 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitro-D-galacto-hept-1-enitol 
• 35800-09-0 7-deoxy-7-nitro-L-glycero-L-galactoheptitol hexaacetate 
• 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 

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.].

Synthesis of N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids

The synthesis of 10 N-(fluoren-9-ylmethoxycarbonyl)glycopyranosylamine uronic acids that are amenable to solid-phase synthesis is described. The general synthetic strategy involves initial incorporation of the protected amine, followed by selective TEMPO oxidation of C-6 hydroxyl groups to give the corresponding Fmoc-protected sugar amino acids. Amine incorporation may be accomplished from aminolysis of the free sugar or from glycosyl azide reduction. The reactions can be carried out on multigram scale, providing access to unique monomer units for future incorporation into combinatorial library syntheses.