The synthesis of the new N-Fmoc-protected dipeptide isoster methyl (IS,2S,5S,6R)-2exo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-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 a-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-azabicyclof 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, alpha-amino acid that may find application in peptidomimetic synthesis
Bicycles Compounds Derived from Tartaric Acid and alpha-Amino acids (BTAa): Synthesis of New Molecular Scaffolds derived from the Combination of (R,R)-Tartaric Acid and L-Serine
Machetti Fabrizio;
2002
Abstract
The synthesis of the new N-Fmoc-protected dipeptide isoster methyl (IS,2S,5S,6R)-2exo-hydroxymethyl-7,8-dioxa-3-azabicyclo[3.2.1]octane-6exo-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 a-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-azabicyclof 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, alpha-amino acid that may find application in peptidomimetic synthesisI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
