189367-63-3

Upstream product

• 4056-11-5 5-azido-5-deoxy-1,2-O-isopropylidene-6-O-tosyl-α-D-glucofuranose 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 55263-78-0 1,2-O-isopropylidene-5-O-tosyl-α-D-glucuronolactone 

Downstream Products

• 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 
• 189367-65-5 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 
• 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 

Relevant academic research and scientific papers

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.