Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/3870
Title: Simple and rapid synthesis of <i>N<sup>α</sup></i><sup>-</sup>urethane protected <i>β</i>-amino alcohols and peptide alcohols employing HATU
Authors: Sureshbabu, Vommina V
Sudarshan, N S
Chennakrishnareddy, G
Keywords: <i>N</i>-Fmoc-<i>β</i>-amino alcohols
Bsmoc-<i>β</i>-amino alcohols
HATU
Issue Date: Apr-2009
Publisher: CSIR
Abstract: The activation of the <i>N<sup>α</sup></i>-urethane protected (Fmoc-/Boc-/Z-/Bsmoc) <i>α</i>-amino acids employing 1-[bis(dimethylamino)­methylene]-1<i>H</i>-1,2,3-triazolo-[4,5-<i>b</i>]pyridinium.0hexa-flurophosphate-3-oxide (HATU) followed by reduction of the <i>in situ </i>generated –OAt ester with NaBH<sub>4</sub> results in the corresponding <i>β</i>-amino alcohols in good yields. This synthesis is the first demonstration of the application of the efficient coupling agent HATU for practical synthesis of<i> β</i>-amino alcohols. The protocol is general for all common <i>N</i>-protecting groups including the highly base sensitive Bsmoc group. The protocol has also been successfully extended for the synthesis of peptide alcohols.
Description: 574-579
URI: http://hdl.handle.net/123456789/3870
ISSN: 0376-4699
Appears in Collections:IJC-B Vol.48B(04) [April 2009]

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