Synthesis and Antiviral Activity of the alpha-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-D-ribohexitol Nucleosides)

Nafizal Hossain; Jef Rozenski; Erik De Clercq; Piet Herdewijn

doi:10.1021/jo961982m

Synthesis and Antiviral Activity of the alpha-Analogues of 1,5-Anhydrohexitol Nucleosides (1,5-Anhydro-2,3-dideoxy-D-ribohexitol Nucleosides)

J Org Chem. 1997 Apr 18;62(8):2442-2447. doi: 10.1021/jo961982m.

Authors

Nafizal Hossain¹, Jef Rozenski, Erik De Clercq, Piet Herdewijn

Affiliation

¹ Rega Institute for Medical Research, Laboratory of Medicinal Chemistry, Minderbroedersstraat 10, B-3000 Leuven, Belgium.

PMID: 11671579
DOI: 10.1021/jo961982m

Abstract

1,5-Anhydro-2,3-dideoxy-D-ribohexitol nucleosides were synthesized starting from 4,6-di-O-benzyl-1,5-di-O-pivaloyl-3-deoxy-D-glucitol using a ring closure procedure. The target nucleoside adopts a (4)C(1) conformation as also demonstrated for the corresponding 1,5-anhydrohexitol nucleosides with beta-configuration of the base-substituted carbon atom. The cytosine congener demonstrated a moderate but selective activity against Herpes simplex virus types 1 and 2.