Add time:09/05/2019         Source:sciencedirect.com

A concise, chiral auxiliary free, methodology for the preparation of orthogonally protected Cα-Methyl Cysteine has been developed. Curtius rearrangement of malonate halfester from PLE hydrolysis (J. Pept. Sci. 2008, 14, 1151; J. Org. Chem. 2003, 68, 5403) and simultaneous Fmoc protection using Titanium(IV) Isopropoxide yielded Fmoc protected amino ester that is then transformed into (R)-NH-Fmoc-S-Trityl-Cα-Methyl Cysteine in three steps. For the synthesis of the S enantiomer of the protected amino acid, enantiomerically enriched CO2-t-Bu half ester derived from PLE hydrolysis was subjected to Curtius reaction followed by Fmoc protection using Titanium(IV) Isopropoxide which is then converted to (S)-NH-Fmoc-S-Trityl-Cα-Methyl Cysteine in two steps.Download full-size image

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