1260792-03-7

Basic information

• Product Name: 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-tetrahydropyranyl-6-O-p-toluenesulfonyl-α-D-glucofuranose
• Synonyms: 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-tetrahydropyranyl-6-O-p-toluenesulfonyl-α-D-glucofuranose
• CAS NO: 1260792-03-7
• Molecular Weight: 460.521
• Mol File: 1260792-03-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-tetrahydropyranyl-6-O-p-toluenesulfonyl-α-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-tetrahydropyranyl-6-O-p-toluenesulfonyl-α-D-glucofuranose(1260792-03-7)
• EPA Substance Registry System: 3-deoxy-3-fluoro-1,2-O-isopropylidene-5-O-tetrahydropyranyl-6-O-p-toluenesulfonyl-α-D-glucofuranose(1260792-03-7)

Safety Data

• Hazardous Substances Data: 1260792-03-7(Hazardous Substances Data)

Upstream product

• 14049-05-9 3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose 
• 18530-81-9 (R)-1-((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 100343-11-1 (R)-2-((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 

Relevant articles and documents

Synthesis of 3-fluoro-6-S-(2-S-pyridyl) nucleosides as potential lead cytostatic agents

The 3-deoxy-3-fluoro-6-S-(2-S-pyridyl)-6-thio-β-d-glucopyranosyl nucleoside analogs 7 were prepared via two facile synthetic routes. Their precursors, 3-fluoro-6-thio-glucopyranosyl nucleosides 5a-e, were obtained by the sequence of deacetylation of 3-deoxy-3-fluoro-β-d-glucopyranosyl nucleosides 2a-e, selective tosylation of the primary OH of 3 and finally treatment with potassium thioacetate. The desired thiolpyridine protected analogs 7a-c,f,g were obtained by the sequence of deacetylation of 5a-c followed by thiopyridinylation and/or condensation of the corresponding heterocyclic bases with the newly synthesized peracetylated 6-S-(2-S-pyridyl) sugar precursor 13, which was obtained via a novel synthetic route from glycosyl donor 12. None of the compounds 6 and 7 showed antiviral activity, but the 5-fluorouracil derivative 7c and particularly the uracil derivative 7b were endowed with an interesting and selective cytostatic action against a variety of murine and human tumor cell cultures.