The use of iodotrimethylsilane in nucleosidation procedure

1 January 1980

journal article
Published by Oxford University Press (OUP) in Nucleic Acids Research

Vol. 8 (20) , 4755-4762
https://doi.org/10.1093/nar/8.20.4755

Abstract

1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-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-beta-D-ribofuranosyl)uracil (III; 89%), with silyated cytosine to afford, on subsequent acetylation, 1-(2,3,5-tri-O-benzoyl-beta-0D-ribofuranosyl)-4-acetamido-2-(1H)-pyrimidinone (IVb; 81%), and with chloromercuri-N-benzoyl-adenine to afford Va and on subsequent debenzoylation, adenosine (Vb; 49%).

Keywords

This publication has 2 references indexed in Scilit:

Silane/iodine-based cleavage of esters and ethers under neutral conditions
Proceedings of the National Academy of Sciences, 1978
The Glycosyl Halides and Their Derivatives
Published by Elsevier ,1955