28235-34-9

Upstream product

• 89157-91-5 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 63-29-6 D-glucurono-6,3-lactone 
• 30694-77-0 3,6-di-O-acetyl-1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranose 
• 4056-11-5 5-azido-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-glucofuranose 
• 108-24-7 acetic anhydride 
• 81969-64-4 1,6-Anhydro-α-L-idohexofuranose 
• 60619-47-8 1,6-anhydro-β-L-idopyranose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 2592-44-1 3-O-acetyl-1,2-O-isopropylidene-5,6-O-di-toluene-p-sulphonyl-α-D-glucofuranose 
• 55263-78-0 1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone 

Relevant academic research and scientific papers

1,6-Anhydro-β-L-hexopyranoses as valuable building blocks toward the synthesis of L-gulosamine and L-altrose derivatives

1,6-Anhydro-β-L-hexopyranoses as valuable building blocks toward the synthesis of L-gulosamine and L-altrose derivatives via the regioselective triflation and benzoylation of 1,6-anhydro β-L-idopyranose followed by SN2 substitution with various

SYNTHESIS OF SOME ARYL 2,3,4,6-TETRA-O-ACETYL-L-IDOPYRANOSIDES AND OF 4-METHYLCOUMARIN-7-YL α-L-IDOPYRANOSIDURONIC ACID

Several routes for synthesis of 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-β-L-idofuranose have been evaluated.Previously described routes, which involved selective sulphonylation, were not reproducible on a 100-g scale.To overcome this difficulty, a new variation was developed, involving complete tosylation of 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone followed by reduction and acetylation.The idofuranose derivative was converted into the desired 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose via 1,6-anhydro-β-L-idopyranose.Fusion of 1,2,3,4,6-penta-O-acetyl-α-L-idopyranose with 4-nitrophenol, 1- or 2-naphtol, or 4-methylcoumarin-7-ol, using freshly fused zinc chloride as catalyst, gave an anomeric mixture of glycosides, with the α anomer being preponderant.The major 4-methylcoumarin-7-yl glycoside was deacylated and converted, by catalytic oxidation, into 4-methylcoumarin-7-yl α-L-idopyranosiduronic acid, fluorogenic substrate for α-L-iduronidase.

1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose

The title compound 13 is prepared on different routes from suitable benzyl derivatives with gluco-configuration.Preparations use the susceptibility of axial 5-O-benzyl groups in this compounds to selective hydrogenolysis, thus allowing subsequent inversion of configuration in this position from D-gluco to L-ido by an oxidation/reduction sequence.Only 0.08percent of 13 are found in the equilibrium mixture of idose in acidic medium.It is shown with 4-C-methyltalose as example, that the amount of 1,6-anhydrofuranoses in these equilibria rises significantly by changing the hydroxy groups in 4-position from secondary to tertiary ones.