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

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

References

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• 15a

  X-ray intensity data of compound 10 was collected on a Bruker SMART APEX CCD diffractometer with omega and phi scan mode, λ(MoKα) = 0.71073 Å at T = 297 (2) K. All the data were corrected for Lorentzian, polarization, and absorption effects using Bruker’s SAINT and SADABS programs. The crystal structure was solved by direct methods using SHELXS-97 and the refinement was performed by full matrix least squares of F ² using SHELXL-97 Hydrogen atoms were included in the refinement as per the riding model.

• 15b

  Sheldrick, G. M.; SHELX-97 program for crystal structure solution and refinement, University of Göttingen, Germany, 1997.

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: [phone]; e-mail: [e-mail]. ac.uk].