125291-12-5

Basic information

• Product Name: ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• Synonyms: ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• CAS NO: 125291-12-5
• Molecular Weight: 296.295
• Mol File: 125291-12-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate(125291-12-5)
• EPA Substance Registry System: ((3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate(125291-12-5)

Safety Data

• Hazardous Substances Data: 125291-12-5(Hazardous Substances Data)

Upstream product

• 18530-84-2 3-deoxy-3-fluoro-1,2-O-isopropylidene-α-D-xylofuranose 
• 98-88-4 benzoyl chloride 
• 6022-96-4 5-O-benzoyl-α-D-xylofuranose 
• 2595-05-3 Diacetone D-glucose 
• 620630-82-2 1,2 5,6-O-di(isopropylidene)-α-D-allofuranose 
• 70722-99-5 (3aR,5R,6S,6aS)-6-fluoro-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole-5-carbaldehyde 
• 532-20-7 D-xylofuranose 
• 80244-95-7 3,5-di-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose 
• 14049-05-9 3-deoxy-1,2;5,6-di-O-isopropylidene-3-fluoro-α-D-glucofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 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 
• 6698-46-0 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose 
• 6612-91-5 ((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 

Downstream Products

• 20535-13-1 Methyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-β-D-xylofuranosid 
• 917110-29-3 1-(3-deoxy-3-fluoro-β-D-lyxofuranosyl)thymine 
• 917110-29-3 3'-deoxy-3'-fluoro-5-methyl-1-β-D-xylofuranosyluracil 
• 158980-88-2 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-fluoro-β-D-xylofuranosyl)thymine 
• 125291-16-9 N2-acetyl-9-(5-O-benzoyl-2,3-dideoxy-3-fluoro-β-D-xylofuranosyl)guanine 

Relevant articles and documents

Synthesis and evaluation of 3′-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents

Kinetoplastid parasites are the causative agents of neglected tropical diseases with an unmet medical need. These parasites are unable to synthesize the purine ring de novo, and therefore rely on purine salvage to meet their purine demand. Evaluating purine nucleoside analogs is therefore an attractive strategy to identify antikinetoplastid agents. Several anti-Trypanosoma cruzi and anti-Trypanosoma brucei 7-deazapurine nucleosides were previously discovered, with the removal of the 3′-hydroxyl group resulting in a significant boost in activity. In this work we therefore decided to assess the effect of the introduction of a 3′-fluoro substituent in 7-deazapurine nucleosides on the anti-kinetoplastid activities. Hence, we synthesized two series of 3′-deoxy-3′-fluororibofuranosyl and 3′-deoxy-3′-fluoroxylofuranosyl nucleosides comprising 7-deazaadenine and -hypoxanthine bases and assayed these for antiparasitic activity. Several analogs with potent activity against T. cruzi and T. brucei were discovered, indicating that a fluorine atom in the 3′-position is a promising modification for the discovery of antiparasitic nucleosides.

Studies on the synthesis of nicotinamide nucleoside and nucleotide analogues and their inhibitions towards CD38 nadase

Nicotinamide adenine dinucleotide (NAD) analogues inhibit the NADase activity of CD38. In the current study, efficient protocols for the synthesis of substituted-nicotinamide nucleosides and nucleotides were developed. The one-pot phosphorylation-esterification strategy provides a convenient way of obtaining nicotinamide nucleoside phosphodiesters from the corresponding nucleosides. Structure-activity relationship information revealed that replacement of 3'-hydroxy group with F or N3 led to the considerably decrease of activity as compared with ara-F NMN. Phosphodiesterification of nicotinamide nucleosides lowers their inhibitory activities in some extent.

Synthesis of a 2,3-dideoxy-2,3-difluorofuranose with the D-lyxo configuration. An intramolecular rearrangement of methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-D-lyxofuranoside observed during the attempted synthesis of 1-(2,3-dideoxy-2,3-difluoro-β-D-lyxof

A new sugar, methyl 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-D-lyxofuranoside (8), which features fluorine substituents on adjacent carbon positions above the plane of the tetrahydrofuran ring, was synthesized from 1,2:5,6-di-O-isopropylidene-α-D-allofuranose