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Synthesis 2008(11): 1783-1787  
DOI: 10.1055/s-2008-1067016
PAPER
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of β-C-Allyl- and β-C-Propargyl-d-arabino­furanosides

C. V. Ramana*, Sachin B. Narute, Rajesh G. Gonnade, Rahul S. Patil
National Chemical Laboratory, Pune 411 008, India
Fax: +91(20)25902629; e-Mail: vr.chepuri@ncl.res.in;
Further Information

Publication History

Received 30 October 2007
Publication Date:
11 April 2008 (online)

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Abstract

The stereoselective synthesis of β-configured C-allyl- and C-propargyl-d-arabinofuranosides (4,7-anhydro-1,2,3-deoxy-d-gluco-oct-1-enitols and -oct-1-ynitols) was addressed by employing allylation/propargylation of a dialdofuranose under aqueous Barbier reaction conditions and acid-catalyzed furan ring transposition of 5-O-mesyl-manno-oct-7-eno- or 5-O-mesyl-manno-oct-7-ynofuranoside derivatives.

Key words

C-glycoside - d-mannose - Barbier reaction - allylation - propargylation - ring transposition

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16

The crystallographic data of compound 10 has been deposited with the Cambridge Crystallographic Data Centre as deposition No. CCDC 676163. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; e-mail: deposit@ccdc.cam. ac.uk].