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


  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.



Aluminum Lithium Hydride Azide Azido 
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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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