478554-84-6

Upstream product

• 66972-48-3 E-4-bromobut-2-enal dimethyl acetal 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 478554-61-9 1Z,3E-1-(4-methoxybenzyloxy)-4-methoxybuta-1,3-diene 
• 1012309-76-0 syn 3-[3-(4-methoxybenzyloxy)prop-1-enyl]-1,5-dimethyl-benzo[e]-[1,3]dioxepane 
• 104863-81-2 E-4-benzyloxybut-2-enal dimethyl acetal 

Relevant academic research and scientific papers

Thermal/hyperbaric heterocycloaddition of 1,4-dialkoxy-1,3-dienes: The de novo (E,Z) way to sugars

1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudoglycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.

Desymmetization of a meso-allylic acetal by enantioselective conjugate elimination

An unprecedented enantioselective deprotonation/conjugate elimination sequence, which transforms an allylic meso-dioxepane into a chiral diene, is described. The best desymmetrization conditions (ee up to 70%) involve s-BuLi and sparteine at -78 °C in THF.