75414-32-3

Upstream product

• 82569-81-1 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose oxime 
• 82469-69-0 3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide 
• 75414-21-0 3,4,6-tri-O-benzoyl-1,5-anhydro-D-fructose E-oxime 
• 14125-75-8 2,3,4,6-tetra-O-benzoyl-D-hydroxyglucal 

Downstream Products

• 75414-41-4 (6S)-4-benzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 
• 154-58-5 1,5-anhydro-D-glucitol 
• 492-93-3 1,5-anhydro-D-mannitol 
• 75414-42-5 (6S)-6-benzoyloxymethyltetrahydropyran-3,4-dione dioxime 
• 75414-43-6 1,5-D-anhydrofructose 
• 52152-86-0 (2R,6S)-4-benzoyloxy-6-benzoyloxymethyl-2-methoxy-2H-pyran-3(6H)-one 
• 13007-49-3 methyl 3,6-di-O-benzoyl-4-deoxy-α-D-glycero-hex-3-enopyranosid-2-ulose 
• 111718-45-7 C₂₅H₂₂O₆ 
• 111718-45-7 C₂₅H₂₂O₆ 
• 111718-43-5 C₂₄H₂₄O₆ 
• 111718-43-5 C₂₄H₂₄O₆ 
• 111718-47-9 ((2S,5S)-5-hydroxy-5-(2-oxopropyl)-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate 
• 111718-49-1 ((2S,5R)-5-hydroxy-5-(2-oxopropyl)-4-oxo-tetrahydro-2H-pyran-2-yl)methyl benzoate 
• 111718-42-4 (2S,5S)-5-allyl-5-benzoyloxy-2-benzoyloxymethyltetrahydropyran-4-one 

Relevant academic research and scientific papers

Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (-)-bissetone and (-)-palythazine

High-yielding protocols are described to convert d-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and β-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-d-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale.

C-glycosidations of a 2-ketohexosyl bromide with electrophilic, radical, and nucleophilic anomeric carbons

The susceptibility of acylated 2-ketohexosyl halides to Chomologation is demonstrated with the easily accessible tri-O-benzoyl-α-D-arabino-hexos-ulosyl bromide 1 as the model compound. C-Glycosidation with an electrophilic anomeric carbon requires prior c

Sugar Enolones, XVIII. - Stereocontrolled Functionalization at Proanomeric Centres by Photobromination. - A Novel Efficient Access to Oxo- and Oximinoglycosyl Bromides

Suitably O-blocked monosaccharides carrying an electron acceptor group such as an oxo or oximino function next to a proanomeric centre, readily homolyze the corresponding push-pull-substituted C-H bond to give under photobromination conditions the respect

A CONVENIENT ACCESS TO 1,5-ANHYDROKETOSES

A convenient, verstile entry into the 1,5-anhydroketose series is described and their conversion into enolones, enolone oximes and γ-pyrones.