74720-63-1Relevant academic research and scientific papers
Facile synthesis of 3'-C-branched 1,5-anhydrohexitol nucleosides
Hossain, Nafizal,Herdewijn, Piet
, p. 1781 - 1786 (2007/10/03)
The 3'-β-C-branched anhydrohexitol nucleosides have been conveniently synthesised starting from commercially available D-ribose following the reaction sequence: (i) conversion of protected pentofuranose sugar to the corresponding hexopyranosyl nitrosugar (ii) addition of the conjugate base of nitrosugar to formaldehyde to obtain C-branched nitro sugar (iii) removal of nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to build up the nucleobase.
Synthesis of 3'-C-branched 1',5'-anhydromannitol nucleosides as new antiherpes agents
Hossain, Nafizal,Van Halbeek, Herman,De Clercq, Erik,Herdewijn, Piet
, p. 2209 - 2226 (2007/10/03)
A series of 3'-β-C-branched anhydromannitol nucleosides were conveniently synthesized starting from commercially available D-ribose. The reaction sequences were: (i) conversion of the protected pentofluranose to the corresponding nitrohexopyranose; (ii) addition of the conjugated base of the nitrosugar to formaldehyde; (iii) removal of the nitro group by n-tributyltin hydride treatment and (iv) Mitsunobu type alkylation to introduce the nucleobase. The conformation of intermediates and final compounds were deduced from NMR analysis. The thymine congener showed potent activity against herpes simplex virus (HSV).
PREPARATION OF 4,6-O-BENZYLIDENE-3-DEOXY-3-C-NITRO-D-GLUCAL AND D-ALLAL AND 1,5-ANHYDRO-4,6-O-BENZYLIDENE-2,3-DIDEOXY-3-C-NITRO-D-threo-HEX-2-ENITOL
Sakakibara, Tohru,Nomura, Yutaka,Sudoh, Rokuro
, p. 53 - 62 (2007/10/02)
Oxidation of 1,5-anhydro-D-mannitol with sodium metaperiodate, followed by nitromethane cyclization and benzylidenation afforded 1,5-anhydro-3-nitrohexitol derivatives having the D-gluco, D-manno, and D-galacto configurations.Conversion of the nitro alcoh
Stereochemistry of Nucleophilic Addition Reactions. VIII. Preparation of 1,5-Anhydro-4,6-O-benzylidene-2,3-dideoxy-3-nitro-D-erythro-hex-2-enitol and Its Reactions with Some Nucleophiles
Sakakibara, Tohru,Nomura, Yutaka,Sudoh, Rokuro
, p. 1642 - 1646 (2007/10/02)
The title compound was synthesized from 1,5-anhydro-D-glucitol via nitromethane cyclization.The reduction of the compound with sodium borodeuteride afforded a mixture of saturated nitro compounds having an axial and equatorial deuterium atom at C-2 in an
