Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Determination of the Anomeric Configurations of 2,3,4,6-Tetra-O-Acetyl-d-Mannopyranosyl Azide

Kelly L. Cosgrove A , Paul V. Bernhardt A , Benjamin P. Ross A and Ross P. McGeary A B C
+ Author Affiliations
- Author Affiliations

A School of Molecular and Microbial Sciences, University of Queensland, Brisbane QLD 4072, Australia.

B School of Pharmacy, University of Queensland, Brisbane QLD 4072, Australia.

C Corresponding author. Email: r.mcgeary@uq.edu.au

Australian Journal of Chemistry 59(7) 473-476 https://doi.org/10.1071/CH06157
Submitted: 10 May 2006  Accepted: 28 June 2006   Published: 22 August 2006

Abstract

The structures of 2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl azide and 2,3,4,6-tetra-O-acetyl-β-d-mannopyranosyl azide were determined using X-ray crystallographic and one-dimensional NOESY techniques.


Acknowledgments

We thank Dr Tri Le for help with one-dimensional NOESY experiments, and Mr Peter Moyle for helpful discussions.


References


[1]   Z. Gyorgdeak, Z. Hadady, N. Felfoldi, A. Krakomperger, V. Nagy, M. Toth, A. Brunyanszki, T. Docsa, P. Gergely, L. Somsak, Bioorg. Med. Chem. 2004, 12,  4861.
        | CrossRef |   open url image1

[2]   O. Lockhoff, Y. Hayauchi, J. Carbohydr. Chem. 2000, 19,  603.
         open url image1

[3]   P. Boullanger, V. Maunier, D. Lafont, Carbohydr. Res. 2000, 324,  97.
        | CrossRef |   open url image1

[4]   Z. Gyorgdeak, L. Szilagyi, H. Paulsen, J. Carbohydr. Chem. 1993, 12,  139.
         open url image1

[5]   L. Hutley, W. Shurety, F. Newell, R. McGeary, N. Pelton, J. Grant, A. Herington, D. Cameron, J. Whitehead, J. Prins, Diabetes 2004, 53,  3097.
         open url image1

[6]   M. Tanaka, I. Yamashina, Carbohydr. Res. 1973, 27,  175.
        | CrossRef |   open url image1

[7]   L. Szilagyi, Z. Gyorgydeak, Carbohydr. Res. 1985, 143,  21.
        | CrossRef |   open url image1

[8]   H. Paulsen, Z. Gyorgydeak, M. Friedmann, Chem. Ber. 1974, 107,  1568.
         open url image1

[9]   S. K. Maity, S. K. Dutta, A. K. Banerjee, B. Achari, M. Singh, Tetrahedron 1994, 50,  6965.
        | CrossRef |   open url image1

[10]   M. M. Ponpipom, R. L. Bugianesi, T. Y. Shen, Carbohydr. Res. 1980, 82,  141.
        | CrossRef |   open url image1

[11]   Z. Gyorgdeak, H. Paulsen, Liebigs Ann. Chem. 1977,  1987.
         open url image1

[12]   S. Sabesan, S. Neira, Carbohydr. Res. 1992, 223,  169.
        | CrossRef |   open url image1

[13]   M. Karplus, J. Am. Chem. Soc. 1963, 85,  2870.
        | CrossRef |   open url image1

[14]   K. P. R. Kartha, R. A. Field, Tetrahedron 1997, 53,  11753.
        | CrossRef |   open url image1

[15]   W. Pfleiderer, H. Zondler, Chem. Ber. 1966, 89,  3022.
         open url image1

[16]   M. Selkti, R. Kassab, H. P. Lopez, F. Villain, C. De Rango, J. Carbohydr. Chem. 1999, 18,  1019.
         open url image1

[17]   D. P. Temelkoff, P. Norris, M. Zeller, Acta Crystallogr. E 2004, 60,  o1975.
        | CrossRef |   open url image1

[18]   A. J. M. Duisenberg, J. Appl. Cryst. 1992, 25,  92.
        | CrossRef |   open url image1

[19]   L. J. Farrugia, J. Appl. Cryst. 1999, 32,  837.
        | CrossRef |   open url image1

[20]   G. M. Sheldrick, SHELXL-97 1997 (University of Göttingen: Göttingen).

[21]   L. J. Farrugia, J. Appl. Cryst. 1997, 30,  565.
        | CrossRef |   open url image1




* Caution: While concentrating the crude product under high vacuum, a small amount of colorless liquid collected in the cold trap of the vacuum pump. This liquid detonated the following day during disassembly of the cold trap. We suspect that the explosive liquid was diazidomethane, and we strongly recommend that azide ion not be allowed to contact halogenated solvents, even during workup of reactions involving its use. For a discussion of the hazards of diazidomethane, see http://pubs.acs.org/cen/safety/index.html


Rent Article (via Deepdyve) Export Citation Cited By (2)