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Synthesis 2011(21): 3523-3529  
DOI: 10.1055/s-0030-1260218
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Suresh E. Kurhadea,b, Videsh T. Salunkhea, V. Siddaiahb, Debnath Bhuniyaa, 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 ;
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Publication History

Received 20 June 2011
Publication Date:
15 September 2011 (online)

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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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Advinus Publication No. ADV-A-013.

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Advinus Publication No. ADV-A-013.