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(L)-(Trimethylsilyl)alanine Synthesis Exploiting Hydroxypinanone-Induced Diastereoselective Alkylation

(L)-(Trimethylsilyl)alanine Synthesis Exploiting Hydroxypinanone-Induced Diastereoselective Alkylation

A René, N Vanthuyne, J Martinez, F Cavelier

Amino Acids. 2013 Aug;45(2):301-7.

PMID: 23620077

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP4206671	(Iodomethyl)trimethylsilane		4206-67-1	Price

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