Efficient Syntheses of Pyrofolic Acid and Pteroyl Azide,
Reagents for the Production of Carboxyl-Differentiated
Derivatives of Folic Acid
Jin Luo
Michael D. Smith
Douglas A. Lantrip
Susan Wang
P. L. Fuchs
10.1021/ja971568j.s003
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
Reaction of folic acid (<b>1</b>) with excess
trifluoroacetic anhydride provides access to both the
previously
unknown <i>N</i><sup>10</sup>-(trifluoroacetyl)pyrofolic acid
(<b>8) </b>and pyrofolic acid (<b>9</b>). Reaction of
either of these materials with
hydrazine selectively affords pteroyl hydrazide (<b>13</b>), which
may be oxidized to pteroyl azide (<b>27) </b>on a large
scale
(62% overall from <b>1</b> without the need for chromatography).
Treatment of <b>27</b> with differentially protected
glutamates
provides a convenient and high-yielding synthesis of differentially
protected, optically pure folates.
1997-10-22 00:00:00
Efficient Syntheses
pteroyl hydrazide
trifluoroacetic anhydride
pyrofolic acid
pteroyl azide
differentially
Pteroyl Azide
folic acid