Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU
The activation of the Nα--urcihanc protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing l-[bis(dimethylamino)- methylene]-lH-l,2,3-triazolo-[4,5-6]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated -OAt ester with NaBH 4 results in the corresponding ss-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of ss-amino alcohols. The protocol is general for all common N-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.
Synthesis of Fmoc-protected β-amino alcohols and peptidyl alcohols from Fmoc-amino acid/peptide acid azides
An efficient synthesis of Nα-9H-fluoren-9- ylmethoxycarbony(Fmoc)-β-amino alcohols by the reduction of Fmoc-α-amino acyl azides employing aqueous NaBH4 as a reducing agent has been described. The reduction is found to be simple and almost complete. All the Fmoc-β-amino alcohols prepared are fully characterized by 1H and 13C NMR and mass spectrometry. Further, the method is extended for the reduction of seven Fmoc-dipeptidyl acids to the corresponding alcohols. Their reduction is also found to be smooth and complete.
Babu, Vommina V. Suresh,Kantharaju,Sudarshan, Naremaddepalli S.
p. 1880 - 1886
(2007/10/03)
Synthesis of Nα-protected peptide acids by the N→ C chain extension employing O,N-bis-trimethylsilyl-amino acids using the mixed anhydride method
Synthesis of Nα-protected peptide acids employing N→C extension strategy using in situ generated X-NH-CHR′-CO-O-CO- iBu and O,N-bis-trimethylsilyl-amino acids has been accomplished. The coupling is very rapid and efficient. The yield
Tantry, Subramanyam J.,Babu, Vommina V. Suresh
p. 1282 - 1287
(2007/10/03)
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