A New 2 H ‐Azirin‐3‐amine as a Synthon for  α ‐Methyl Glutamate | Zendy

Hilty Florentine M. | Zendy; Brun Kathrin A. | Zendy; Heimgartner Heinz | Zendy

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A New 2 H ‐Azirin‐3‐amine as a Synthon for α ‐Methyl Glutamate

Author(s) -

Hilty Florentine M.,

Brun Kathrin A.,

Heimgartner Heinz

Publication year - 2004

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.200490226

Subject(s) - synthon , chemistry , diastereomer , dipeptide , amine gas treating , stereochemistry , protecting group , block (permutation group theory) , side chain , amino acid , organic chemistry , biochemistry , alkyl , geometry , mathematics , polymer

The synthesis of a novel 2,2‐disubstituted 2 H ‐azirin‐3‐amine 10 as a building block for racemic Glu(2Me) is described. This synthon contains an ester group in the side chain. The reaction of 10 with thiobenzoic S ‐acid and the amino acid Z‐Val‐OH yielded the racemic monothiodiamide 17 and the dipeptide 18 as a mixture of diastereoisomers, respectively ( Scheme 2 ). From 18 , each of the protecting groups was removed selectively ( Scheme 3 ).

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