54946-48-4

Upstream product

• 59556-69-3 2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose 
• 50-69-1 D-ribose 
• 100-51-6 benzyl alcohol 
• 532-20-7 D-Ribose 
• 100-39-0 benzyl bromide 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 1927-62-4 tetrahydro-2-(benzyloxy)-2H-pyran 
• 55797-81-4 O²,O³,O⁵-Tribenzoyl-D-ribose 
• 135246-59-2 1′-O-benzyl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranoside 

Downstream Products

• 59556-69-3 2,3,5-tri-O-benzoyl-1-O-benzyl-β-D-ribofuranose 
• 1195430-42-2 benzyl-[O⁵-(toluene-4-sulfonyl)-β-D-ribofuranoside] 
• 122315-13-3 benzyl-[O²,O⁵-bis-(toluene-4-sulfonyl)-β-D-ribofuranoside] 
• 103266-47-3 benzyl-[tris-O-(toluene-4-sulfonyl)-β-D-ribofuranoside] 
• 122174-79-2 benzyl-(O²,O³-carbonyl-O⁵-diphenoxyphosphoryl-β-D-ribofuranoside) 
• 117363-13-0 benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranoside 
• 78416-50-9 Benzyl-2,3-di-O-acetyl-5-O-(triphenylmethyl)-β-D-ribofuranosid 
• 103702-73-4 (2R,3R,4S,5R)-2-Benzyloxy-5-trityloxymethyl-tetrahydro-furan-3,4-diol 
• 77886-95-4 C₂₆H₂₄O₇ 
• 23276-32-6 benzyl 2,3-O-isopropylidene-D-ribofuranoside 
• 233667-77-1 (2R,3R,4S,5R)-2-Benzyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3,4-diol 
• 135246-59-2 1′-O-benzyl-2′,3′,5′-tri-O-acetyl-β-D-ribofuranoside 
• 854646-85-8 1-(5'-O-methyl-β-D-ribofuranosyl)-2-methylbenzimidazole-2'-phenylphosphate 
• 64018-52-6 1-benzyl-2:3-O-isopropylidene-5-O-methyl-β-D-ribofuranoside 

Relevant academic research and scientific papers

Synthesis of a 3′-Fluoro-3′-deoxytetrose Adenine Phosphonate

A new synthetic route to a 3′-fluoro-3′-deoxytetrose adenine phosphonate has been developed. The synthesis starts from l-xylose and key steps include the stereospecific introduction of the phosphonomethoxy group and adenine. In addition, a regioselective

An unexpected rearrangement of pent-4-enofuranosides to cyclopentanones upon hydrogenolysis of the anomeric benzyl group

During our synthesis toward the unique nucleoside antibiotic A201A, we were surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.

Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates

Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates is reported. This process is catalyzed by triphenylphosphine and tetrabromomethane at room temperature under neutral conditions. With this operationally simple protocol thermodynamically favored, glycosides were obtained in a very straightforward reaction.

Synthesis of alkylcarbonate analogs of O-acetyl-ADP-ribose

The non-hydrolyzable alkylcarbonate analogs of O-acetyl-ADP-ribose have been synthesized from the phosphorylated ribose derivatives after coupling with AMP morpholidate promoted by mechanical grinding. The analogs were assessed for their ability to inhibi

Kinetic solvent deuterium isotope effect in transesterification of RNA models

2-Methylbenzimidazole ribonucleoside arylphosphates (1a,b) and alkylphosphates (2a,b) were synthesized as RNA model compounds containing a minimised number of exchangeable protons. Intramolecular transesterification of these substrates was studied in H2O and D2O solutions over a wide pL range and apparent kinetic solvent deuterium isotope effects of the alkaline cleavage of both substrates and of the cleavage and isomerisation of 2a under neutral and acidic conditions were determined. The observed K H2O/kD2O of 4.9 obtained for the alkaline cleavage of the arylphosphate 1b can be primarily attributed to the ΔpK of the attacking nucleophile. The alkyl leaving group in 2a brings about an additional 1.5-fold isotope effect (kH2O/kD2O of 7.1 observed), which, considering the pL-dependence of the reaction, can not be explained by a process involving a proton transfer. Differences in solvation of the transition state are tentatively suggested as a source of the difference. In contrast to alkaline cleavage, under neutral and acidic conditions the cleavage and isomerisation of 2a showed no apparent solvent isotope effect. Several examples found in the literature show that intramolecular proton transfer from phosphate to the leaving group in pre-equilibria may not necessarily result in an observable solvent isotope effect. This may also explain the results obtained in the present work, since intramolecular proton transfer processes take place in transesterification reactions of 2a under neutral and acidic conditions. Relevance of the results obtained in the base catalysed cleavage to hammerhead ribozyme reaction is briefly discussed. Copyright

Method for producing a beta-D-ribofuranose derivative or an optical isomer thereof

The invention provides a method for efficiently producing β-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzyl-β-D-ri

Readily available carbohydrate-derived imines and amides as chiral ligands for asymmetric catalysis

An easy and diastereoseletive strategy for the synthesis of a new tetrahydrofuranic chiral aldehyde and a new tetrahydrofuranic acid derived from D-ribose is reported. These compounds have been shown to be useful starting materials for obtaining a never d

Method for producing beta-D-ribofuranose derivatives or optical isomers thereof

The present invention provides a method for efficiently producing β-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzy

Synthesis and properties of flavin ribofuranosides and flavin ribopyranosides

Ribose-containing coenzymes like flavin mononucleotide (FMN) can be considered to be fossils of a prebiotic RNA world in which RNA encoded genetic information and catalyzed chemical reactions. To investigate the catalytic and base-pairing properties of FM

A One-pot Glycosylation of Tetrahydropyranyl (THP) Ether Intermediates

Tetrahydropyranyl (THP) derivatives of alcohols are converted in one-pot and in stereoselctive manner into the corresponding 1-O-alkyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosides on treatment with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose and trimethyls