A Phosphine-Mediated Synthesis
of 1,4-Oxazepine- and 1,5-Oxazocine-Based Sugar Hybrids from Deoxysugar
Azides

Suresh E. Kurhade; Videsh T. Salunkhe; V. Siddaiah; Debnath Bhuniya; D. Srinivasa Reddy

doi:10.1055/s-0030-1260218

PAPER

A Phosphine-Mediated Synthesis of 1,4-Oxazepine- and 1,5-Oxazocine-Based Sugar Hybrids from Deoxysugar Azides [¹]

Suresh E. Kurhade^a,b, Videsh T. Salunkhe^a, V. Siddaiah^b, Debnath Bhuniya^a, D. Srinivasa Reddy*^a,c
^a Discovery Chemistry, Advinus Therapeutics Ltd., Quantum Towers, Plot No. 9, Rajiv Gandhi Infotech Park, Phase-I, Hinjewadi, Pune 411057, India
^b Department of Organic Chemistry, Andhra University, Visakhapatnam 530003, India
^c National Chemical Laboratory (CSIR, India), Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India
Fax: +91(20)66539620; e-Mail: ds.reddy@ncl.res.in ;

Abstract

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Abstract

An efficient and convenient method was developed for the synthesis of novel 1,4-oxazepine- and 1,5-oxazocine-based sugar hybrids from readily available deoxysugar azides by means of tributylphosphine-mediated tandem reactions. The resulting glycoconjugates might be useful in increasing the diversity of sugar backbones, and could find applications as potential glycomimetics and in drug discovery.

Key words

tandem reactions - heterocycles - carbohydrates - alkynes - oxazepines - oxazocines - azides

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Supplementary Material

Supporting Information