75414-32-3

Basic information

• Product Name: 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose
• Synonyms: 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose
• CAS NO: 75414-32-3
• Molecular Weight: 474.467
• Mol File: 75414-32-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose(75414-32-3)
• EPA Substance Registry System: 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose(75414-32-3)

Safety Data

• Hazardous Substances Data: 75414-32-3(Hazardous Substances Data)

Upstream product

• 82569-81-1 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose oxime 
• 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 
• 82469-69-0 3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide 

Downstream Products

• 82469-69-0 3,4,6-tri-O-benzoyl-α-D-arabino-hexopyranosyl-2-ulose bromide 
• 82469-69-0 C₂₇H₂₁BrO₈ 
• 75414-38-9 (6S)-4-benzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 
• 75414-36-7 3,4,6-tri-O-benzoyl-1,5-anhydro-D-fructose diethyldithioacetal 
• 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 
• 75414-41-4 (6S)-4-benzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 
• 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 

Relevant articles and documents

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.

Beweis der (S,S)-Konfiguration von (-)-Bisseton durch Synthese aus D-Glucose

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Eine stereospezifische Synthese von (S,S)-Palythazin aus D-Glucose

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