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Nucleic Acids Research, 1980, Vol. 8, No. 20 4755-4762
© 1980

CHEMISTRY

The use of iodotrimethylsilane in nucleosidation procedure+

Zdenek Tocik, Robert A. Earl++ and Jirí Bernek

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences 166 10 Prague 6, Czechoslovakia

Received August 6, 1980.

1-0-Acetyl-2,3,5-tri-O-benzoyl-ß-D-ribofuranose (I) was reacted with iodotrimethylsilane (II) and the product, the glycosyl iodide, was coupled with silylated uracil to afford 1-(2,3,5-tri-O-benzoyl-ß-D-ribofuranosyl) uracil (III; 89%), with silylated Cytosine to afford, on subsequent acetylation, 1-(2,3,5-tri-O-benzoyl-ß-D-ribofuranosyl)-4-acetamido-2(1H)-pyrimidinone (IVb; 81%), and with chloromercuri-N-benzoyl-adenine to afford Va and on subsequent debenzoylation, adenosine (Vb; 49%).

+Part XXIX in the Series Analogues of Nucleosides; Part XXVIII, Collect.Czech.Chem.Commun.45, 599–605 (1980).

++The procedure was proposed end initiated by R.A. Earl from The University of Utah, Salt Lake City during his short visit (1978) to the Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences under the auspices of the U.S. National Academy of Sciences and Czechoslovak Academy of Sciences.


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