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Synthesis of N-protected N-methyl serine and threonine

✍ Scribed by Yue Luo; Ghotas Evindar; Dan Fishlock; Gilles A Lajoie


Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
71 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis


Two efficient and convenient syntheses of N-Cbz and N-Fmoc N-methyl serine and threonine are described. The amino acid side-chain alcohol can be protected as a TBDMS ether in very good yield or left free, followed by the formation and subsequent reduction of the corresponding oxazolidinone.


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The reactivity of electrophiles derived from N-tritylserine, threonine and allothreonine esters toward a selection of nucleophiles was investigated. Best yields from substitution products were obtained with N-trityliodoalanine and soft nucleophiles such as thiols. This strategy was applied to the sy