178680-28-9

Upstream product

• 87-72-9 L-(+)-arabinose 
• 589-18-4 4-Methylbenzyl alcohol 

Downstream Products

• 178680-27-8 4'-methylbenzyl 3,4-O-isopropylidene-β-L-arabinopyranoside 
• 178680-25-6 Acrylic acid (3aS,6S,7R,7aS)-2,2-dimethyl-6-(4-methyl-benzyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 

Relevant academic research and scientific papers

Sugarometallic chemistry: Aglycone-chromium complex as chiral auxiliary in asymmetric Diels-Alder reaction

The diastereoselectivity of the Diels-Alder reaction of η6-(4'-methylbenzyl 2-O-Acryloyl-3,4-O-isopropylidene-β-L-arabinopyranoside) tricarbonylchromium(0) 5 with isoprene, butadiene, cyclopentadiene, and furan were studied, and the best select

Catalytic asymmetric epoxidation of alkenes with arabinose-derived uloses

Four L-erythro-2-uloses were readily prepared from L-arabinose via a reaction sequence involving Fischer glycosidation, acetalization and oxidation. Bulky steric sensors at the anomeric center could enhance the stereoselectivity of the dioxirane epoxidation and one of the uloses performed with good enantioselectivity towards trans-stilbene (up to 90% ee). However, the catalysts decomposed during the epoxidation and the maximum chemical yield was only 13% under the basic conditions. Three L-threo-3-uloses could overcome the decomposition problem based on the electron withdrawing effect of the ester group(s) α to the ketone functionality. The best chemical yield was up to 93% using a ketone with two flanking ester groups. One of the improved uloses displayed moderate enantioselectivity towards trans-disubstituted and trisubstituted alkenes (40-68% ee).