182216-96-2Relevant academic research and scientific papers
Amino acid based diastereoselective synthesis of fucosamines
Ruiz, Maria,Ojea, Vicente,Quintela, Jose M.
, p. 1535 - 1549 (2007/10/03)
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.
Amino acid based diastereoselective synthesis of elsaminose
Ruiz, Maria,Ojea, Vicente,Quintela, Jose Ma.
, p. 5743 - 5746 (2007/10/03)
Optically pure (+)-elsaminose (2), the amino sugar contained in the antitumor antibiotic elasmicin A, has been synthesized in eight steps (26% overall yield) from known building blocks derived from glycine, L-valine, and L-threonine. Direct and selective construction of the key intermediate 6, with the complete backbone and the proper stereochemical configuration, is accomplished by a syn-aldol type reaction between lithiated Schollkopf's bislactime ether 5 and a 1,3-dioxolane-4-carboxaldehyde (-)-3.
