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Article Dans Une Revue Amino Acids Année : 2013

(L)-(Trimethylsilyl)alanine synthesis exploiting hydroxypinanoneinduced diastereoselective alkylation

Résumé

A new and efficient synthesis of (L)-(trimethylsilyl) alanine (TMSAla) with suitable protection for use in Solid Phase Peptide Synthesis (SPPS) has been accomplished starting from glycine tert-butyl ester and using hydroxypinanone as chiral inductor. The silylated side chain was introduced by alkylation of the Schiff base intermediate with iodomethyl(trimethylsilane) at -78 C. Among the different synthetic routes that were tested including several chiral inductors and different Schiff bases, this strategy was selected and afforded (L)-TMSAla in good chemical overall yield with 98 % ee.

Dates et versions

hal-00852031 , version 1 (19-08-2013)

Identifiants

Citer

A. René, N. Vanthuyne, J. Martinez, F. Cavelier. (L)-(Trimethylsilyl)alanine synthesis exploiting hydroxypinanoneinduced diastereoselective alkylation. Amino Acids, 2013, 45, pp.301-307. ⟨10.1007/s00726-013-1492-2⟩. ⟨hal-00852031⟩
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