%0 Journal Article
%A Luo, Jin
%A Smith, Michael D.
%A Lantrip, Douglas A.
%A Wang, Susan
%A Fuchs, P. L.
%D 1997
%T Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide,
Reagents for the Production of Carboxyl-Differentiated
Derivatives of Folic Acid
%U https://acs.figshare.com/articles/journal_contribution/Efficient_Syntheses_of_Pyrofolic_Acid_and_Pteroyl_Azide_Reagents_for_the_Production_of_Carboxyl-Differentiated_Derivatives_of_Folic_Acid/3666111
%R 10.1021/ja971568j.s002
%2 https://ndownloader.figshare.com/files/5755839
%K Efficient Syntheses
%K pteroyl hydrazide
%K trifluoroacetic anhydride
%K pyrofolic acid
%K pteroyl azide
%K differentially
%K Pteroyl Azide
%K folic acid
%X Reaction of folic acid (1) with excess
trifluoroacetic anhydride provides access to both the
previously
unknown N10-(trifluoroacetyl)pyrofolic acid
(8) and pyrofolic acid (9). Reaction of
either of these materials with
hydrazine selectively affords pteroyl hydrazide (13), which
may be oxidized to pteroyl azide (27) on a large
scale
(62% overall from 1 without the need for chromatography).
Treatment of 27 with differentially protected
glutamates
provides a convenient and high-yielding synthesis of differentially
protected, optically pure folates.
%I ACS Publications