23276-32-6

Basic information

• Product Name: 1-O-Benzyl-2-O,3-O-isopropylidene-β-D-ribofuranose
• Synonyms: 1-O-Benzyl-2-O,3-O-isopropylidene-β-D-ribofuranose;Benzyl 2-O,3-O-isopropylidene-β-D-ribofuranoside
• CAS NO: 23276-32-6
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.3163
• Mol File: 23276-32-6.mol

Chemical Properties

• Boiling Point: 398.6°Cat760mmHg
• Flash Point: 194.8°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 4.56E-07mmHg at 25°C
• Refractive Index: 1.559
• CAS DataBase Reference: 1-O-Benzyl-2-O,3-O-isopropylidene-β-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-Benzyl-2-O,3-O-isopropylidene-β-D-ribofuranose(23276-32-6)
• EPA Substance Registry System: 1-O-Benzyl-2-O,3-O-isopropylidene-β-D-ribofuranose(23276-32-6)

Safety Data

• Hazardous Substances Data: 23276-32-6(Hazardous Substances Data)

Usage

Type of compound

chemical compound

Derivative of

ribofuranose (a type of sugar)

Common usage

organic synthesis and carbohydrate chemistry

Characterized by

a benzyl group attached to the 1-position of the ribofuranose ring, and an isopropylidene group at the 2and 3-positions

Function

protecting group for the hydroxyl (OH) functional groups on the ribofuranose ring in chemical reactions

Role

important intermediate in the synthesis of various nucleosides, nucleotides, and other bioactive compounds.

InChI:InChI=1/C15H20O5/c1-15(2)19-12-11(8-16)18-14(13(12)20-15)17-9-10-6-4-3-5-7-10/h3-7,11-14,16H,8-9H2,1-2H3

Upstream product

• 10257-32-6 D-ribose 
• 67-64-1 acetone 
• 100-51-6 benzyl alcohol 
• 54946-48-4 benzyl-β-D-ribofuranoside 
• 869354-98-3 benzyl 2,3: 5,6-di-O-isopropylidene-D-mannofuranoside 
• 869353-20-8 benzyl 2,3-O-isopropylidene-D-mannofuranoside 
• 100-44-7 benzyl chloride 
• 3458-28-4 D-Mannose 
• 1042431-16-2 (3aS,4S,6aS)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 
• 532-20-7 D-Ribose 
• 50-69-1 D-ribose 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 75921-19-6 Benzyl-5-O-tert-butyldimethylsilyl-2,3-O-isopropyliden-β-D-ribofuranosid 
• 64018-52-6 1-benzyl-2:3-O-isopropylidene-5-O-methyl-β-D-ribofuranoside 
• 189275-81-8 {[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-hydroxy-phosphorylmethyl}-phosphonic acid mono-((3aR,4R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl) ester 
• 98391-41-4 benzyl 5-azido-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 1294499-30-1 (3R,4S,5S)-1-(tert-butoxycarbonyl)-4,5-O-isopropylidene-3-O-(p-tolylsulfonyl)-3,4,5-trihydroxypiperidine 
• 1294499-35-6 (3S,4R,5R)-5-(benzylamino)-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4-dihydroxypiperidine 
• 1294499-39-0 (3S,4R,5R)-5-O-benzyl-1-(tert-butoxycarbonyl)-3,4-O-isopropylidene-3,4,5-trihydroxypiperidine 
• 1294499-40-3 (3R,4S,5S)-3-O-benzyl-1-(tert-butoxycarbonyl)-3,4,5-trihydroxypiperidine 
• 1294499-41-4 (3R,4R,5S)-3-O-benzyl-1-(tert-butoxycarbonyl)-3,4,5-trihydroxypiperidin-3,4-yl sulfite 
• 54946-49-5 1-O-benzyl-2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-β-D-ribofuranose 
• 1314088-78-2 ethyl (2S,3S,4R,5S)-1-benzyl-3,4-isopropylidenedioxy-5-methylpyrrolidine-2-acetate 
• 1314088-64-6 benzyl 5-bromo-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 102854-76-2 (3aS,6R,6aS)-4-Benzyloxy-6-methoxymethoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole 

Relevant articles and documents

Structure-property relationships of ribose based ionic liquids

The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.

Nucleophilic (Radio)Fluorination of Redox-Active Esters via Radical-Polar Crossover Enabled by Photoredox Catalysis

We report a redox-neutral method for nucleophilic fluorination of N-hydroxyphthalimide esters using an Ir photocatalyst under visible light irradiation. The method provides access to a broad range of aliphatic fluorides, including primary, secondary, and tertiary benzylic fluorides as well as unactivated tertiary fluorides, that are typically inaccessible by nucleophilic fluorination due to competing elimination. In addition, we show that the decarboxylative fluorination conditions are readily adapted to radiofluorination with [18F]KF. We propose that the reactions proceed by two electron transfers between the Ir catalyst and redox-active ester substrate to afford a carbocation intermediate that undergoes subsequent trapping by fluoride. Examples of trapping with O- and C-centered nucleophiles and deoxyfluorination via N-hydroxyphthalimidoyl oxalates are also presented, suggesting that this approach may offer a general blueprint for affecting redox-neutral SN1 substitutions under mild conditions.

Synthesis of 4-amino-4,5-dideoxy-L-lyxofuranose derivatives and their evaluation as fucosidase inhibitors

The nitrone 4 (4,5-dideoxy-4-hydroxylamino-3,4-O-isopropylidene-L- lyxofuranose) was synthesised from d-ribose and used as key intermediate for the preparation of fucosidase inhibitors. We describe two transformations of 4. Hydrolysis with aqueous sulfur

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

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

Benzyl 2,3-O-isopropylidene-β-D-ribo-1,4-pentodialdofuranoside as a D-Ribose Chiron for the Synthesis of Terpenyl Tetraols and Aminotriols

Wittig condensation of title compound with a phosphorane derived from R-(+)-limonene followed by catalytic hydrogenation, provided a C-5 extended ribofuranose derivative, a model intermediate for the synthesis of terpenyl tetraols, via NaBH4 reduction, an

Simple Approach to O-Protected Deaminotunicaminyluracil

A five-step synthesis of deaminotunicaminyluracil is presented.Coupling of the ylide, generated from the phosphonium salt 4, with the aldehyde 5 afforded the undecose 6 in high yield.The key step in this synthesis was the hydroboration-oxidation reaction of the olefin 6.For this purpose several hydroborating reagents were examined.The diborane-THF reagent led to the desired deaminotunicamine derivative 8, as the predominant product.Condensation of undecose 8c with 1,3-di-O-trimethylsilyluracil gave the title compound.

AN EFFICIENT SYNTHESIS OF (2S,3R)- AND (2S,3S)-SPHINGOSINE

A straightforward sequence of reactions allows the conversion of D(+)-Mannose and D(+)-ribono-1,4-lactone into "erythro"-(2S,3R)- and "threo"-(2S,3S)-sphingosine, respectively.

Nucleosides. 114. 5'-O-Glucuronides of 5-Fluorouridine and 5-Fluorocytidine. Masked Precursors of Anticancer Nucleosides

5'-O-Glucuronides of anticancer nucleosides, 5-fluorouridine and 5-fluorocytidine, were synthesized by three different methods.The best preparative procedure was the one starting from benzyl 5-O-(methyl-2',3',4'-tri-O-acetyl-β-D-glucopyranosyluronate)-2,3