186694-63-3

Upstream product

• 100-39-0 benzyl bromide 
• 186694-54-2 (3R,6S,1'R,2'S,3'R)-3-(1-benzyloxy-2,3-isopropylidenedioxybutyl)-2,5-diethoxy-3,6-dihydro-6-isopropylpyrazine 
• 182216-93-9 (R)-((2R,5S)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-((4R,5R)-2,2,5-trimethyl-[1,3]dioxolan-4-yl)-methanol 
• 186694-55-3 ethyl (2R,3R,4S,5R)-2-amino-3-benzyloxy-4,5-isopropylidenedioxyhexanoate 
• 186694-57-5 ethyl (2R,3R,4S,5R)-3-benzyloxy-2-[N-(benzyloxycarbonyl)amino]-4,5-isopropylidenedioxyhexanoate 

Downstream Products

• 186694-68-8 (3R,4R,5S,1'R)-4-benzyloxy-3-[N-(benzyloxycarbonyl)amino]-5-[1-(isopropyldimethylsilanyloxy)ethyl]tetrahydrofuran-2-one 

Relevant academic research and scientific papers

Amino acid based diastereoselective synthesis of fucosamines

Enantiomerically pure (+)-D-fucosamine 1, (+)-N-methyl-D-fucosamine 2 and (+)-3-O-methyl-D-fucosamine 3 (elsaminose) have been synthesised from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 8 was accomplished by a highly syn,anti-selective aldol reaction between lithiated Schoellkopf's bis-lactim ether 7 and the 1,3-dioxolane-4-carboxaldehyde 5. Elaboration of the common intermediate required optional methylation, selective hydrolysis of the bis-lactim ether in the presence of an isopropylidene ketal, lactonization and partial reduction of the carboxylic group.

Asymmetric Synthesis of D-Fucosamine and N-Methyl-D-Fucosamine

(+)-D-fucosamine and (+)-N-methyl-D-fucosamine (the amino sugar moiety of neocarzinostatin) have been synthesized from known building blocks derived from natural amino acids. Direct and diastereoselective construction of the key intermediate 4 was accomplished by a syn-aldol type reaction between Sch?llkopf's bislactim ether 2 and the 1,3-dioxolane-4-carboxaldehyde 3. Reduction and monomethylation of a O'Donnell's Schiff base derived from the common amino ester 7 allows an optional access to the N-methyl derivative.