Tetrahedron Letters p. 5409 - 5412 (1995)
Update date:2022-07-31
Topics:
Fischer, Peter M.
Sandosham, Jessie
New procedures for the preparation of allothreonine, suitably protected for solid phase peptide synthesis, were developed.Stereochemical inversion in the side chain of threonine via thionyl chloride-induced oxazoline cyclisation and subsequent hydrolysis, followed by protection of the allothreonine amino and hydroxyl functions provided Fmoc-D-alloThr(But)-OH from benzoyl-D-threonine phenacyl ester in only five steps.Alternatively, it was shown that temporary carboxyl protection for introduction of the t-butyl ether group can be circumvented by direct selective ester acidolysis from Fmoc-Thr(But)-OBut.
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