%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/3666117 %R 10.1021/ja971568j.s003 %2 https://acs.figshare.com/ndownloader/files/5755845 %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