58394-32-4

Usage

Type of compound

Rare sugar compound

Usage

Synthesis of various bioactive compounds

Molecular structure

Six-membered ring sugar molecule with a double bond between the second and third carbons

Biological properties

Potential antiviral and antibacterial activities

Pharmaceutical applications

Development of novel pharmaceuticals

Organic synthesis

Used as a chiral building block

Availability

Limited

Ongoing research

Exploring potential applications in pharmaceuticals and biochemistry

Upstream product

• 21193-75-9 D-galactal 
• 33647-85-7 isolevoglucosenone 
• 58238-42-9 1,6-anhydro-3-deoxy-β-D-threo-hexopyranos-4-ulose 
• 58394-31-3 1,6-anhydro-2,3-dideoxy-β-D-erythro-hex-2-enopyranose 
• 33648-08-7 (-)-(1R,4R,5R)-7,8-Dioxabicyclo[3.2.1]oct-3-en-2-yl acetate 
• 29514-09-8 (1R,2S,4S,5R)-6,8-dioxabicyclo[3.2.1]octane-2,4-diol 
• 58238-45-2 1,6-anhydro-2,3-dideoxy-β-D-erythro-hexopyranos-2-ulose 
• 52630-80-5 (+/-)-7,8-Dioxabicyclo[3.2.1]oct-3-en-2-ol 
• 1487-18-9 (furan-2-yl)ethylene 
• 2873-29-2 D-glucal triacetate 
• 50705-28-7 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 58238-41-8 C₆H₆O₄ 
• 37112-31-5 levoglucosenone 
• 34147-09-6 1,6:3,4-dianhydro-β-D-talopyranose 

Downstream Products

• 50705-28-7 1,6-anhydro-3,4-dideoxy-β-D-threo-hex-3-enopyranose 
• 141054-99-1 1,6-anhydro-4-O-benzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose 
• 33647-85-7 isolevoglucosenone 
• 331633-91-1 1,6-anhydro-4-O-p-methoxybenzyl-2,3-dideoxy-β-D-threo-hex-2-enopyranose 
• 331633-94-4 1,6:2,3-dianhydro-2,3-epithio-4-O-p-methoxybenzyl-β-D-talopyranose 
• 331633-92-2 1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose 
• 331633-93-3 1,6-anhydro-4-O-p-methoxybenzyl-β-D-gulopyranose 2,3-cyclic sulfate 
• 331633-97-7 1,6-anhydro-2-azido-2-deoxy-3-S-(2,4-dinitrophenyl)-4-O-p-methoxybenzyl-3-thio-β-D-galactopyranose 
• 82742-16-3 1,6:2,3-Dianhydro-4-O-benzyl-β-D-glucopyranose 
• 61074-28-0 1,6:2,3-di-anhydro-4-O-benzyl-β-D-talopyranose 
• 59464-21-0 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-galactopyranose 
• 174905-26-1 3-O-Acetyl-1,6-anhydro-4-O-benzyl-2-bromo-2-deoxy-β-D-galactopyranose 

Relevant academic research and scientific papers

Manipulating the enone moiety of levoglucosenone: 1,3-Transposition reactions including ones leading to isolevoglucosenone

The manipulation of the enone moiety associated with the biomass-derived, homochiral and now abundant compound levoglucosenone (1) is described. While the trichloroacetimidates derived from the allylic alcohols 3 and 4 failed to engage in Overman-type rea

The conversion of levoglucosenone into isolevoglucosenone

Levoglucosenone (1), a compound that will soon be available in tonne quantities through the pyrolysis of acid-treated lignocellulosic biomass, has been converted into isolevoglucosenone (2) using Wharton rearrangement chemistry. Treatment of compound 1 with alkaline hydrogen peroxide gave the γ-lactones 5 and 6 rather than the required epoxy-ketones 3 and/or 4. However, the latter pair of compounds could be obtained by an initial Luche reduction of compound 1, electrophilic epoxidation of the resulting allylic alcohol 8 and oxidation of the product oxiranes 9 and 10. Independent treatment of compounds 3 and 4 with hydrazine then acetic acid followed by oxidation of the ensuing allylic alcohols finally afforded isolevoglucosenone (2). Details of the single-crystal X-ray analyses of epoxy-alcohols 9 and 10 are reported.

Chemoselective elaboration of O-linked glycopeptide mimetics by alkylation of 3-thioGalNAc

A critical branch point in mucin-type oligosaccharides is the β1 → 3 glycosidic linkage to the core α-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a

Lipase-mediated preparation of enantiopure isolevoglucosenone

A route to enantiopure isolevoglucosenone, a regioisomer of levoglucosenone and a potential chiral building block, has been developed by employing lipase-mediated kinetic resolution as the key step.

Reactions of 2-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-ene with diethylaminosulfur trifluoride and with halogens. Facile synthesis of 1,6- anhydrohalohexopyranoses

D-Galactal 1 reacts in THF in the presence of catalytic amounts of concentrated sulfuric acid to give (2R)-2-hydroxy-6,8-dioxabicyclo[3.2.1]oct- 3-ene (4) in a Ferrier-type rearrangement in 40% yield. When 4 is treated with diethylaminosulfur trifluoride