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.
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 / CINI N; MACHETTI F; MENCHI G; OCCHIATO E G; A. GUARNA. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - ...:(2002), pp. 873-880.
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
MACHETTI, FABRIZIO;MENCHI, GLORIA;OCCHIATO, ERNESTO GIOVANNI;GUARNA, ANTONIO
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 synthesis.File | Dimensione | Formato | |
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