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Title: Simple and rapid synthesis of Nα-urethane protected β-amino alcohols and peptide alcohols employing HATU
Authors: Sureshbabu, Vommina V
Sudarshan, N S
Chennakrishnareddy, G
Keywords: N-Fmoc-β-amino alcohols;Bsmoc-β-amino alcohols;HATU
Issue Date: Apr-2009
Publisher: CSIR
Abstract: The activation of the Nα-urethane protected (Fmoc-/Boc-/Z-/Bsmoc) α-amino acids employing 1-[bis(dimethylamino)­methylene]-1H-1,2,3-triazolo-[4,5-b]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the in situ generated –OAt ester with NaBH4 results in the corresponding β-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of β-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.
Page(s): 574-579
ISSN: 0376-4699
Appears in Collections:IJC-B Vol.48B(04) [April 2009]

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