4056-11-5

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 55263-78-0 1,2-O-isopropylidene-5-O-tosyl-α-D-glucuronolactone 
• 63-29-6 D-glucurono-6,3-lactone 
• 3067-56-9 D-glucurono-3,6-lactone acetonide 
• 69465-27-6 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 55263-78-0 1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone 

Downstream Products

• 30694-77-0 3,6-di-O-acetyl-1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranose 
• 189367-63-3 Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 
• 28235-34-9 2,3,4-tri-O-acetyl-1,6-anhydro-β-L-idopyranose 
• 189367-66-6 Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-((R)-4-oxo-azetidin-2-yloxy)-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester 
• 189367-64-4 Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-[(3aR,5S,6S,6aR)-6-(1-ethoxy-ethoxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester 
• 189367-65-5 Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aR,5S,6S,6aR)-2,2-dimethyl-6-vinyloxy-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 

Relevant academic research and scientific papers

Synthesis of 5,6-dimodified open-chain D-fructose derivatives and their properties as substrates of bacterial polyol dehydrogenase

5-Deoxy-5-fluoro-D-xylulose as well as a range of new 5,6-dimodified open-chain analogues of D-fructose, namely the 5,6-diazido-5,6-dideoxy, 6-azido-5,6-dideoxy, 6-azido-5,6-dideoxy-5-fluoro, 5,6-dideoxy-5-fluoro, 5,6-dideoxy-6-fluoro and 5,6-dideoxy-5,6-

Synthesis of a 1-oxacephem structurally related to clavulanic acid from D-glucuronolactone

[2+2]Cycloaddition of chlorosulfonyl isocyanate to 3-O-vinyl ethers derived from D-glucose and D-glucuronolactone proceeded with an excellent stereoselectivity to provide azetidin-2 ones with (R) configuration at C-4'. Intramolecular N-alkylation afforded 1-oxabicyclic β-lactams having six- or seven-membered ring fused to the four-membered one.

Control of regioselectivity in reactions of dialkylstannylene acetals. Part I. A dramatic reversal of regioselectivity in mono-p-toluenesulfonation reactions

The regioselectivities of p-toluenesulfonation reactions of dialkylstannylene acetals obtained from a number of carbohydrate-derived terminal 1,2-diols in the absence of added nucleophiles have been explored as functions of the carbohydrate structure, the

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.