𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Hydrolysis of 2′-deoxypurine nucleosides. The effect of substitution at the C-8 position

✍ Scribed by Ali Laayoun; Jean-Luc Décout; Jean Lhomme

Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
217 KB
Volume
35
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Modification of purine nucleosides at C-8 has been thoroughly studied in the search for antieaacer and antiviral agents, and for introducing labe1s.t Sttbstltution at C-8 mod&~ the hydrolytic stability of the nucleoside, a property that has been studied for some ribotmcleosides2 and 2'-3'dideoxyderivatives.~ The purine 2'-deoxyribonuclcosides, however, have received less attcntion.~ WC mport some new nucleusii designed as probes (7.8) or for Iinking active agents (3dIl-14). sad dcacribe th& hyd&ytic stability. ~~ucti~ofihothiogroupindtea'aeoxyadenosiaeaod2'~~~land9&~~3 and11was~~~byaatiagthe~~~and1~pvithhrcfrogta~inD~.~?hethiaetbers 4-6,12-W werr. obtained by alkylation of the thiolates genem&d with potassium carbonate in DMF with the wrresponding 1-halogenoakmes. Oxidakn of the thioether l2 using m-CPBA in ethanol led to cw

📜 SIMILAR VOLUMES

Synthesis of novel tetracycline derivati
Synthesis of novel tetracycline derivatives with substitution at the C-8 position
✍ Phaik-Eng Sum; Ving J. Lee; Francis P. Tally 📂 Article 📅 1994 🏛 Elsevier Science 🌐 French ⚖ 148 KB

I-Substituted te.mcycm. otiho&bmam' meS, ticatalyzed azide rearrangements. 7(or 9)-azimyclines Abstract llwC-8 funcdooalizatiooof te~clinederivatives via acid-catalyzed reatIangemf%It Of 7(or 9)azieyclines is c%zscribed. These ccmpomaaretbefifsttobepreparedfmulanin~ttehacyclincnucleus.

A direct method for the alkylation of ad
A direct method for the alkylation of adenosine nucleosides at position 8.
✍ Derek H.R. Barton; Charles J.R. Hedgecock; Edgar Lederer; William B. Motherwell 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 118 KB

Alkylation of adenosine derivatives at carbon 8 can be conveniently achieved by lithiation followed by reaction with an alkyl halide. Selective methods for the direct modification of purine nucleoside derivatives are surprisingly few in number.

Asymmetric synthesis of polyfunctionaliz
Asymmetric synthesis of polyfunctionalized piperidines: substitution at the C-4 position
✍ Florence Billon-Souquet; Thierry Martens; Jacques Royer 📂 Article 📅 1999 🏛 Elsevier Science 🌐 French ⚖ 228 KB

The electrochemical bis-bromination of the chiral building block 1 followed by a dehydrobromination step allowed the preparation of a bromopiperideine 3. The stereoselective addition of nucleophiles onto this key intermediate permitted the synthesis of various 4-substituted piperidine derivatives.

Modification of the 2′-position of purin
Modification of the 2′-position of purine nucleosides: syntheses of 2′-α-substituted-2′-deoxyadenosine analogs
✍ R. Ranganathan 📂 Article 📅 1977 🏛 Elsevier Science 🌐 French ⚖ 291 KB

Nucleoside analogs with stereochemical and/or functional group modifications in the sugar residue have shown promise as anti-tumor, 1 anti-viral, or immunosuppressive agents. In addition to these properties, adenosine analogs have been of interest as hypotensive agents, as inhibitors of platelet agg