Synthesis of Enantiomerically Pure 1,2-Diamine Derivatives of
7-Azabicyclo[2.2.1]heptane. New Leads as Glycosidase Inhibitors
and Rigid Scaffolds for the Preparation of Peptide Analogues
Antonio J. Moreno-Vargas
Catherine Schütz
Rosario Scopelliti
Pierre Vogel
10.1021/jo0301088.s002
https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Enantiomerically_Pure_1_2-Diamine_Derivatives_of_7-Azabicyclo_2_2_1_heptane_New_Leads_as_Glycosidase_Inhibitors_and_Rigid_Scaffolds_for_the_Preparation_of_Peptide_Analogues/3698238
Enantiomerically pure alcohols (−)- and (+)-7-<i>tert</i>-butoxycarbonyl-6-<i>endo</i>-<i>p</i>-toluenesulfonyl-7-azabicyclo[2.2.1]hept-2-en-5-<i>endo</i>-ol ((−)-<b>11</b> and (+)-<b>11</b>) have been obtained from the Diels−Alder
adduct of <i>N</i>-(<i>tert</i>-butoxycarbonyl)pyrroel and 2-bromo-1-<i>p</i>-toluenesulfonylacetylene, including a
resolution method. These two alcohols were converted into (+)- and (−)-5-<i>exo</i>-amino-7-(<i>tert</i>-butoxycarbonyl)-2,3-<i>exo</i>-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane ((+)-<b>18 </b>and (−)-<b>18</b>) and (+)-
and (−)-5-<i>endo</i>-amino-7-(<i>tert</i>-butoxycarbonyl)-2,3-<i>exo</i>-isopropylidenedioxy-7-azabicyclo[2.2.1]heptane
((+)-<b>19</b> and (−)-<b>19</b>) after adequate functionalization and desulfonylation steps. The corresponding
conformationally constrained bicyclic 1,2-diamines (+)-<b>4</b>, (−)-<b>4</b>, (±)-<b>5</b>, (±)-<b>6</b>, (+)-<b>7</b>, and (−)-<b>7</b> were
obtained from the protected precursors <b>18</b> and <b>19</b> and evaluated as glycosidase inhibitors. Diamines
(+)-<b>4</b>, (−)-<b>4</b>, (+)-<b>6</b>, and (−)-<b>6</b> can be seen as new nonpeptide molecular scaffolds for the design of
peptide analogues.
2003-06-10 00:00:00
tert
butoxycarbonyl
Rigid Scaffolds
endo
Glycosidase Inhibitors
peptide analogues
isopropylidenedioxy
resolution method
Peptide Analogues Enantiomerically
desulfonylation steps
exo
Diamine
precursors 18
glycosidase inhibitors