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For a related approach
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70349980498
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note
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Within the limits of our NMR and UPLC detection methods the couplings reported in this manuscript proceed without racemization. In preliminary studies on the thioacid-sulfonamide method, and on the related thioacid-amine-Sangers/ Mukaiyama approach, this was rigorously established through the synthesis of authentic samples of epimeric products.[6a, 7]
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33
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70349979791
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note
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With cesium carbonate the N-FNS protected di- and higher peptide thioacids were observed by mass spectrometry to undergo cyclization, with retention of the FNS group, rather than condensation when exposed to a DNS peptide and cesium carbonate. This was attributed to the acidity of the FNS sulfonamide NH group and so was circumvented by the use of the milder base. The use of pyridine as base afforded a similar result to cesium carbonate.
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