Stereoselective Synthesis of Orthogonally Protected 1,2-Diaminoinositols from D-Mannose

abstract

We present herein a promising novel strategy for the transformation of sugar aldehydes into 1,2-diaminoinositols. This process, based on the sequential intermolecular aza-Henry reaction and intermolecular Henry reaction allowed the total synthesis of a 1,2-diaminoinositols with total stereochemical control. The new route constitutes a simpler and more efficient approach than those previously described routes to 1,2-diaminoinositols and it has the additional advantage of offering the possibility of orthogonal protection of the amino groups.

keywords

ONE-POT SYNTHESIS; ABSOLUTE-CONFIGURATION; DERIVATIVES; 1,2-DIAMINES; CHEMISTRY; MODEL

subject category

Chemistry

authors

Acurcio, RC; Soengas, RG; Paz, FAA; Silva, AMS

our authors

acknowledgements

Thanks are due to the University of Aveiro, Fundacao para a Ciencia e a Tecnologia (FCT), European Union, QREN, FEDER, and COMPETE for funding the Organic Chemistry Research Unit (project PEst-C/QUI/UI0062/2013), the Associated Laboratory CICECO (Pest-C/CTM/LA0011/2013) and the Portuguese National NMR Network (RNRMN). R.S. thanks the FCT for an 'Investigador Auxiliar' position.

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