55263-78-0

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 20513-98-8 1,2-O-isopropylidene-α-D-glucofuranurono-6,3-lactone 
• 63-29-6 D-glucurono-6,3-lactone 
• 104-15-4 toluene-4-sulfonic acid 

Downstream Products

• 30694-75-8 Toluene-4-sulfonic acid (3aR,3bS,6R,6aS,7aR)-5-hydroxy-2,2-dimethyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-6-yl ester 
• 4056-11-5 5-azido-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-glucofuranose 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 
• 110522-67-3 C₇₂H₆₆O₆ 
• 110522-68-4 C₆₄H₆₂O₆ 
• 110522-66-2 (2S,3S,4S,5S)-2,5-Bis-benzyloxy-1,6-bis-trityloxy-hexane-3,4-diol 
• 62102-44-7 2,3,4,5-tetra-O-benzyl-D-ido-hexodialdose 
• 110522-70-8 3,4-di-O-allyl-2,5-di-O-benzyl-L-ido-hexodialdose 
• 110522-69-5 (2S,3R,4R,5S)-3,4-Bis-allyloxy-2,5-bis-benzyloxy-hexane-1,6-diol 
• 110522-64-0 (2S,3S,3aS,5S,6R,6aS)-3,6-Bis-benzyloxy-2,5-dimethoxy-hexahydro-furo[3,2-b]furan 
• 94926-00-8 2,5-di-O-benzyl-L-iditol 
• 62102-45-8 2,3,4,5-tetra-O-benzyl-L-iditol 
• 488-45-9 L-iditol 
• 73892-50-9 6-O-benzoyl-1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-(6R)-α-D-gluco-hexodialdo-1,4:6,3-difuranose 

Relevant academic research and scientific papers

Synthesis of Optically Active Inositol Derivatives Starting from D-Glucurono-6,3-lactone

D-Glucurono-6,3-lactone was converted to optically active and partially protected inositols.The synthetic strategy involves an efficient conversion of the D-gluco configuration to the L-ido configuration and dials to cyclitols.

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.

A novel synthesis of 5-thio-D-glucose

A shorter synthesis of 5-thio-D-glucose is described in 8 steps from commercially available D-glucofurano-3,6-lactone.