1373390-69-2

Upstream product

• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 108149-63-9 tert-butyl (4S)-4-(hydroxymethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 95715-87-0 (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine 
• 1373390-61-4 ethyl (4RS,5R,6R)-5-(tert-butoxycarbonyl)amino-4-hydroxy-6-(4-methoxybenzoxy)-2-methylene-7-octenoate 
• 1373390-65-8 ethyl (3R,4R,5R)-4-(tert-butoxycarbonyl)amino-5-hydroxy-(4-methoxybenzoxy)-1-cyclohexenecarboxylate 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 1373390-54-5 ethyl (3R,4S,5R)-4-(tert-butoxycarbonyl)amino-3-hydroxy-5-methanesulfonyloxy-1-cyclohexenecarboxylate 
• 1373390-70-5 ethyl (3aS,7aS)-3H-4-(4-methoxybenzoxy)-2-oxo-3a,4,7,7a-tetrahydrobenzoxazolidine-6-carboxylate 

Relevant academic research and scientific papers

Transformation of d-serine to highly functionalized cyclohexenecarboxylates in study of oseltamivir synthesis

In an attempted synthesis of oseltamivir, D-serine was used to prepare (R)-Garner aldehyde, which reacted with vinylzinc reagent to give an alcohol product predominating in the (1′R,4S)-isomer. After the alcohol was protected as p-methoxybenzyl ether, the N,O-acetal was hydrolyzed and oxidized to an aldehyde, which underwent Reformatsky-type reaction with ethyl α-(bromomethyl)acrylate by promotion of indium to give an addition product readily for ring-closure metathesis to afford 3-alkoxy-4-amido-5-hydroxy-1- cyclohexenecarboxylates. After activation of the 5-hydroxy group as methanesulfonate, an attempted substitution reaction with sodium azide gave unexpectedly a cyclic carbamate via an intramolecular nucleophilic attack of the 4-tert-butoxycarbamate group.