Elsevier

Tetrahedron Letters

Volume 35, Issue 17, 25 April 1994, Pages 2645-2646
Tetrahedron Letters

The use of tetramethylguanidinium azide in non-halogenated solvents avoids potential explosion hazards

https://doi.org/10.1016/S0040-4039(00)76995-4Get rights and content

Abstract

Tetramethylguanidinium azide was used in the quantitative conversion of glycosyl halides 1 – 5 to the corresponding glycosyl azides 10 – 14. The stereoselective reactions occurred with complete inversion at the anomeric centers. The titled reagent was also employed in the selective synthesis of pseudoglycosyl azide 16 and two steroidal azides 17 and 18. All reactions were carried out in non-halogenated solvents to avoid potential explosion hazards.

Tetramethylganidinium azide was used in the efficient synthesis of glycosyl azides and steroidal azides in non-halogenated solvents, thereby avoiding potential explosion hazards.

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References (4)

  • C. Li et al.

    Tetrahedron Lett.

    (1993)
  • N.P. Peet et al.

    Chem. & Engr. News

    (April 9, 1993)
    V.J. Hruby et al.

    Chem. & Engr. News

    (Oct. 11, 1993)
    A. Hassner et al.

    J. Org. Chem.

    (1990)
There are more references available in the full text version of this article.

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