Synthetic aspects of folate conjugates
Abstract
Reaction of folic acid 1.1 with excess trifluoroacetic anhydride provides access to both the previously unknown N10-trifluoroacetyl pyrofolic acid 1.7 and pyrofolic acid 1.8. Reaction of either of these materials with hydrazine selectively affords pteroyl hydrazide 2.12 which may be oxidized to pteroylazide 5.11 on large scale (62% overall from 1.1 without the need for chromatography). Treatment of 5.11 with differentially protected glutamates provides a convenient and high-yielding synthesis of differentially protected, optically pure folates.
Degree
Ph.D.
Advisors
Fuchs, Purdue University.
Subject Area
Organic chemistry
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