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Volume :15 Issue : 1 1988      Add To Cart                                                                    Download

Attempted synthesis of nucleosides by fusion of heterocyclic bases with protected sugar derivatives

Auther : KHAWLA I. SHAKlR, NAHLAH M. AL-SAKKAL AND

 

Department of Chemistry, College of Science, Al-Mustansiriyah University, Baghdad, Iraq.

 

ABSTRACT

 

The aim of this work is to propose a new method for adding a molecule of a heterocyclic

compound to a sugar molccule to form new compounds which might possess some biological importance due to thc structural similarities to known antibiotics. The method involves an S,2 accommod3tion of the attacking group (pyridine derivatives) in a sugar molecule (ribofuranoside derivative) carrying a labile group (tosyl). The work describes two main reactions leading to the formation of two new products, as well as a detailed analysis of the products using n.m.r.. i.r. and elemental analysis in addition to the usual identification techniques. 2-Aminodihydropyridinyl and 4-aminodihydropyridinyl T.3-0-isopropylidene-5-0-acetyl-b-D-ribofuranoses, ( I ) and (2) respectively, were prepared by substitution of the tosyl group present on the anomeric centre of the sugar molecule by the bases.

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