427882-59-5

Upstream product

• 427882-48-2 methyl (2R,3R)-(-)-N-benzyl-N-[(1R)-1-benzyloxymethyl-2-hydroxyethyl]-2,3-di-O-isopropylidenetartramate 
• 427882-49-3 methyl (2R,3R)-(-)-N-benzyl-N-[(1S)-1-benzyloxymethyl-1-formylmethyl]-2,3-di-O-isopropylidenetartramate 
• 427882-47-1 methyl (2S)-2-(benzoylamino)-3-benzyloxypropanoate 
• 170956-48-6 (2R)-(+)-2-(N-benzylamino)-3-benzyloxy-1-propanol 
• 98-88-4 benzoyl chloride 
• 427882-51-7 (-)-methyl (1R,4S,5S,7R)-3-benzyl-4exo-(O-benzylhydroxymethyl)-2-oxo-6,8-dioxa-3-azabicyclo[3.2.1]octane-7exo-carboxylate 

Downstream Products

• 427882-60-8 (-)-methyl (1S,2S,5S,6R)-3-benzyl-2exo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-carboxylate 

Relevant academic research and scientific papers

Bicyclic compounds derived from tartaric acid and α-amino acids (BTAas): Synthesis of new molecular scaffolds derived from the combination of (R,R)-tartaric acid and L-serine

The synthesis of the new N-Fmoc-protected dipeptide isoster methyl (1S,2S,5S,6R)-2exo-hydroxymethyl-7,8-dioxa-3-azabicyclo [3.2.1] octane-6 exo-carboxylate (BTS) has been achieved, starting from (R,R)-tartaric acid and O-benzyl-L-serine, in 11% overall yield after 9 steps. Interestingly, starting from the same α-amino acid, it was also possible to prepare the 2endo-substituted compound, formally derived from the combination of tartaric acid with D-serine. Each compound has a CH2OH functional group at C-2, which is very useful for greater diversification of the 7,8-dioxa-3-azabicyclo [3.2.1]octane-6-carboxylate (BTAa) dipeptide isosters. The oxidation of the C-2 carbinol group in BTS, moreover, gave rise to a novel, conformationally constrained, α-amino acid that may find application in peptidomimetic synthesis.