59090-41-4

Basic information

• Product Name: 5-acetyl-1-(2-deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 59090-41-4
• Molecular Formula: C₁₁H₁₄N₂O₆
• Molecular Weight: 270.2387
• Mol File: 59090-41-4.mol
• Article Data: 4

Chemical Properties

• Density: 1.517g/cm³
• Refractive Index: 1.593
• CAS DataBase Reference: 5-acetyl-1-(2-deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-acetyl-1-(2-deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione(59090-41-4)
• EPA Substance Registry System: 5-acetyl-1-(2-deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione(59090-41-4)

Safety Data

• Hazardous Substances Data: 59090-41-4(Hazardous Substances Data)

Upstream product

• 6214-65-9 5-acetyluracil 
• 951-78-0 2'-deoxyuridine 
• 61135-33-9 2'-deoxy-5-ethynyluridine 
• 3056-12-0 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride 

Relevant articles and documents

Ethynyl side chain hydration during synthesis and workup of "clickable" oligonucleotides: Bypassing acetyl group formation by triisopropylsilyl protection

Clickable oligonucleotides with ethynyl residues in the 5-position of pyrimidines (ethdC and ethdU) or the 7-position of 7-deazaguanine (ethc7Gd) are hydrated during solid-phase oligonucleotide synthesis and workup conditions. The side products were identified as acetyl derivatives by MALDI-TOF mass spectra of oligonucleotides and by detection of modified nucleosides after enzymatic phosphodiester hydrolysis. Ethynyl → acetyl group conversion was also studied on ethynylated nucleosides under acidic and basic conditions. It could be shown that side chain conversion depends on the nucleobase structure. Triisopropylsilyl residues were introduced to protect ethynyl residues from hydration. Pure, acetyl group free oligonucleotides were isolated after desilylation in all cases.

THE SYNTHESIS AND CRYSTAL STRUCTURE OF 5-ACETYL-2'-DEOXYURIDINE

5-Acetyl-2'-deoxyuridine (1) has been synthesised by treating 2'-deoxy-5-ethynyluridine with dilute sulphuric acid.Condensation of the trimethylsilyl derivate of 5-acetyluracil with 2-deox-3,5-di-O-p-toluoyl-α-D-erythropentofuranosyl chloride gave a mixture of α- and β-anomeric blocked nucleosides from which the α-anomer was isolated and the p-toluoyl groups removed to give 5-acetyl-1-(α-D-2-deoxyerythropentofuranosyl)uracil.Only a poor yield of the β-anomer (1) was obtained by this procedure.The UV spectra and m.p. obtained for 1 differed from the values quoted in the literature.The crystals of 1 are monoclinic, space group P21, with a=9.525, b=12.16, c=5.22 Angstroem, β=92.03 deg and two molecules in the unit cell.The structure was refined by least-squares calculations to R 3.4percent for 1426 observed counter amplitudes.The pyrimidine ring is essentially planar with the acetyl group inclined at 6 deg to it.The sugar ring has the highly unusuael C(4')-exo conformation and the arrangement about C(4')-C(5') is such that O(5') is oriented gauche with respect to both O(1') and C(3').The glycosidic torsion angle O(1')-C(1')-N(1)-C(6) is 56 deg (anti conformation).