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Synthesis of desoxy derivatives of β-1,6-anhydro-D-glucopyranose (levoglucosan)

  • N. M. Merlis
  • E. A. Andrievskaya
  • L. I. Kostelian
  • O. P. Golova
Organic and Biological Chemistry

Conclusions

  1. 1.

    A study was made of the nucleophilic replacement of the hydroxyl groups in the partial tosyl esters of levoglucosan by treatment with triphenyl phosphite methiodide. When β-l,6-anhydro-2-O-tosyl-D-glucopyranose is reacted with this reagent the reaction goes selectively to give 4-iodo-4-desoxy-2-O-tosyl-β-D-1,6-anhydrogalactopyranose.

     
  2. 2.

    The 3- and 2-desoxy derivatives of levoglucosan were synthesized by opening the α-oxide rings in 4-O-benzyl-α-1,6∶2,3-dianhydro-D-allopyranose and 4-O-benzyl-β-1,6∶2,3-dianhydro-D-mannopyranose with aluminium lithium hydride.

     

Keywords

Aluminium Ester Hydroxyl Lithium Hydride 
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

  • N. M. Merlis
    • 1
  • E. A. Andrievskaya
    • 1
  • L. I. Kostelian
    • 1
  • O. P. Golova
    • 1
  1. 1.N. D. Zelinskli Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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