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Synthesis of azido derivative from 2(3)-O-tosyl-6-O-tritylcellulose and its conversion to an a minopolysacchride

  • A. I. Usov
  • N. I. Nosova
  • S. I. Firgang
  • O. P. Golova
Organic and Biological Chemistry

Conclusions

  1. 1.

    (2)3-Azido-(2)3-desoxy-6-O-tritylpolysaccharide was synthesized by replacing the tosyloxy groups by azide groups in 2(3)-O-tosyl-6-O-triacetylcellulose in hexamethylphosphoric triamide medium, the reduction of which with aluminum lithium hydride gave a (2)3-amino-(2)3-desoxypolysaccharide with a degree of substitution of 0.5–0.7 in amino groups.

     
  2. 2.

    The tosylation of 6-O-tritylcellulose goes predominantly at C-2. When the degree of substitution of tosyloxy groups is 0.7 the degree of substitution of tosyloxy groups at C-2 is equal to 0.6, and 0.1 at C-3.

     
  3. 3.

    The replacement of tosyloxy groups by azide groups in the 2-O-tosyl-6-O-tritylglucose units of 2(3)-O-tosyl-6-O-tritylcellulose goes predominantly via the formation of 2,3-anhydro rings, the opening of which by the azide anion proceeds mainly via attack at C-3. The reaction proceeds to a lesser degree via the direct replacement of the tosyloxy groups by the azide anion, with an inversion of the configuration at C-2. In contrast, the insertion of azide groups into the 3-O-tosyl-6-O-tritylglucose units proceeds mainly by direct substitution.

     

Keywords

Aluminum Lithium Hydride Azide Azido 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Publishing Corporation 1975

Authors and Affiliations

  • A. I. Usov
    • 1
  • N. I. Nosova
    • 1
  • S. I. Firgang
    • 1
  • O. P. Golova
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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