RING-EXPANDED ANALOGUES OF NATURAL OXETANOCIN: (+) AND (−) HYDROXYMETHYL ISODIDEOXYADENOSINE

New enantiomeric isonucleoside analogues related to natural oxetanocin have been synthesized from D-glucosamine and D-glucose. The structures of the target compounds were confirmed by NMR, HRMS, UV, single crystal X-ray, and optical rotation data. Stability studies with respect to purine nucleoside phosphorylase and adenosine deaminase show that these compounds are not substrates. Antiviral results are discussed.

[1]  V. Nair.  Antiviral Isonucleosides: Discovery, Chemistry and Chemical Biology , 2002 .

[2]  V. Nair,et al.  Homologues of anti‐HIV Active Isodideoxynucleosides. , 1996 .

[3]  L. Boone,et al.  Antiviral, metabolic, and pharmacokinetic properties of the isomeric dideoxynucleoside 4(S)-(6-amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol , 1995, Antimicrobial agents and chemotherapy.

[4]  V. Nair,et al.  Antiviral activities of isometric dideoxynucleosides of D- and L-related stereochemistry , 1995, Antimicrobial agents and chemotherapy.

[5]  S. Spergel,et al.  Synthesis and antiviral activity of novel isonucleoside analogs. , 1993, Journal of medicinal chemistry.

[6]  V. Nair,et al.  Novel, stable congeners of the antiretroviral compound 2',3'-dideoxyadenosine , 1989 .

[7]  T. Takeuchi,et al.  Inhibition of infectivity of human immunodeficiency virus by oxetanocin. , 1987, The Journal of antibiotics.

[8]  J. Watters,et al.  Synthesis of some derivatives of 2,5-Anhydro-D-mannitol , 1983 .

[9]  D. Horton,et al.  The nitrous acid deamination of glycosides and acetates of 2-amino-2-deoxy-D-glucose , 1973 .

[10]  J. Defaye,et al.  Méthanolyse des 1,2-O-isopropylidène-5-O-p-tolylsulfonylpentofuranoses: Influence des facteurs stériques sur la formation des 2,5-anhydropentoses diméthyl acétals☆☆☆★ , 1971 .

[11]  D. Horton,et al.  [Methanolysis of 1,2-O-isopropylidene-5-O-p-tolylsulfonyl-pentofuranoses: influence of steric factors on the formation of 2,5-anhydropentose dimethyl acetals]. , 1971, Carbohydrate research.