259746-16-2

Upstream product

• 27821-03-0 3,6-Anhydro-1,2-O-isopropyliden-α-D-glucofuranose 
• 628292-86-4 Acetic acid (3R,3aS,6R,6aR)-3-(1-acetoxy-1-methyl-ethoxy)-6-benzyloxy-hexahydro-furo[3,2-b]furan-2-yl ester 
• 108-24-7 acetic anhydride 
• 26922-94-1 (1S,3R,4R,5S,8R)-8-benzyloxy-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane 
• 94933-92-3 3-O-Acetyl-1,2-O-isopropyliden-D-glucofuranose-5,6-sulfit 

Downstream Products

• 475558-28-2 1-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-thymine 
• 1000407-11-3 (2R,3R,3aS,6R,6aR)-1-(3-acetoxy-6-benzyloxy-hexahydrofuro[3,2-b]furan-2-yl)-1H-pyrimidine-2,4-dione 
• 259746-18-4 9-(5'-O-benzyl-3',6'-anhydro-β-D-glucofuranosyl)-inosine 
• 259746-17-3 6-chloro-9-(2'-O-acetyl-3',6'-anhydro-5'-O-benzyl-β-D-glucofuranosyl)-purine 

Relevant academic research and scientific papers

First example of 5/6-O-linked pseudosaccharides: synthesis of bicyclic nucleosides containing azido or extended carbohydrate moiety

Treatment of the d-glucose-derived substrate 1 with sodium hydride in tetrahydrofuran provided 3,6-anhydro monosaccharide 2, along with the 5,6-ether linked pseudodisaccharide 3, and pseudotrisaccharide 4. However, reaction of 1 with sodium ethoxide in ethanol afforded 2 as the sole product, elaborated to the bicyclic azidonucleosides 9 and 16. Acetylated bicyclic nucleosides 17-19 with extended carbohydrate residues have been synthesized from 3.

Controlled acetolysis of 3,6-anhydro-5-o-benzyl-1,2-o-isopropylidene-α-D-glucofuranose: Synthesis of 1-(3′,6′-anhydro-α-D-glucofuranosyl)thymine

Controlled acetolysis of 1,2-O-isopropylideneglucofuranose derivative 1 in Ac2O:AcOH:H2SO4 at 0°C is reported to isolate 2-acetoxy dimethylmethylenoxy glucofuranose derivative 2 in quantitative yield. Utility of 2 for the synthesis of alpha linked nucleoside 5a is demonstrated.

Synthesis of 3,6-anhydro sugars from cyclic sulfites and sulfates and their applications in the preparation of bicyclonucleoside analogues of ddC and ddA

Cyclic sulfates 21-23 and sulfite 27 derived from glucofuranose lead to the 3,6-anhydrosugar 28 in excellent yields when treated with sodium sulfite or in basic media. When treated with sodium sulfite, the 3-deoxy derivative 24 fails to give the intramolecular cyclization which leads to the anhydrosugars. Instead it gives the disulfonate derivative 26. 28 was used as starting material to prepare bicyclonucleosides 43 and 46, which are analogues of the anti-HIV agents ddC and ddA.