2008

Amino acidsU 0400 New Convenient Reagents for Chemoselective N-Alkoxycarbonylation of (S)-Iso-

serine: Application in the Isepamicin Synthesis. — A series of N-alkoxycarbonyl mercaptobenzothiazoles (I) is synthesized and successfully applied as reagents for the chemoselective protection of amino groups. It is shown that the reagents are highly ef-fective in the selective N-alkoxycarbonylation of (S)-isoserine (II). The efficiency of compound (Ib) is also demonstrated by the selective protection of the amino groups in position 3 and 6' of gentamicin B [→(IV)] and (S)-isoserine before their peptide cou-pling in the synthesis of the aminoglycoside antibiotic isepamicin. — (DOKTOROV*, K.; TARPANOV, V.; MECHKAROVA, P.; Synth. Commun. 37 (2007) 21, 3709-3718; Inst. Org. Chem., Bulg. Acad. Sci., BG-1113 Sofia, Bulg.; Eng.) — H. Toeppel

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