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Efficient Synthesis of Differentially Protected (S,S)-2,7- Diaminooctanedioic Acid, the Dicarba Analogue of Cystine

✍ Scribed by Meinolf Lange; Peter M. Fischer

Publisher: John Wiley and Sons
Year: 1998
Tongue: German
Weight: 134 KB
Volume: 81
Category: Article
ISSN: 0018-019X
DOI: 10.1002/(sici)1522-2675(19981111)81:11<2053::aid-hlca2053>3.0.co;2-4

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✦ Synopsis

Convenient preparative syntheses of differentially protected forms of (S,S)-2,7-diaminooctanedioic acid (2), suitable for application in peptide chemistry, are described. The key compound, the di-Cbz-protected phenacyl monoester 7a (Cbz [(benzyloxy)carbonyl]), was obtained by means of Schöllkopf bis-lactim ether methodology and optimized monoesterification procedures. Selective amino deprotection at the non-esterified amino-acid function of 7a by dichloromethyl-methyl-ether-induced N-carboxyanhydride formation, and hydrolysis permitted access to the Boc/Cbz-and Fmoc/Cbz-protected monophenacyl esters 11a and 11b, as well as to the fully orthogonally protected Fmoc/Boc monophenacyl ester 12 ( Boc (tert-butoxy)carbonyl, Fmoc (9H-fluoren-9-ylmethoxy)carbonyl).

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