Synthesis of N-protected N-methyl serine and threonine
β 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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β¦ 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.
π SIMILAR VOLUMES
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