2847-00-9

Usage

Uses

Used in Organic Synthesis:
1,2:5,6-Di-O-isopropylidene-alpha-D-ribo-3-hexulofuranose is used as a synthetic building block for the creation of various organic compounds. Its unique structure and properties make it a valuable component in the synthesis of complex molecules, particularly in the fields of pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1,2:5,6-Di-O-isopropylidene-alpha-D-ribo-3-hexulofuranose is used as a key intermediate in the development of novel drug candidates. Its versatility in organic synthesis allows for the creation of a wide range of bioactive molecules with potential therapeutic applications.
Used in Agrochemical Industry:
1,2:5,6-Di-O-isopropylidene-alpha-D-ribo-3-hexulofuranose is also utilized in the agrochemical industry for the synthesis of new pesticides, herbicides, and other crop protection agents. Its unique chemical properties enable the development of innovative compounds with improved efficacy and selectivity.
Used in Materials Science:
In the field of materials science, 1,2:5,6-Di-O-isopropylidene-alpha-D-ribo-3-hexulofuranose is employed in the synthesis of advanced materials with specific properties, such as polymers with tailored characteristics for various applications, including electronics, coatings, and adhesives.

InChI:InChI=1/C12H18O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6,8-10H,5H2,1-4H3/t6-,8-,9-,10-/m1/s1

Upstream product

• 108-24-7 acetic anhydride 
• 57873-10-6 1,2:5,6-di-O-isopropylidene-3-C-<(R,S)-nitro(methoxycarbonyl)methyl>-α-D-allofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 20316-77-2 (3aR,5R,6S,6aR)-6-(allyloxy)-5-((R)-2,2-dimethyl[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxole 
• 2595-05-3 Diacetone D-glucose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 876938-53-3 Cyclohepta-1,3-diene 
• 266306-47-2 3-chloro-3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-nitroso-α-D-glucofuranose 
• 492-62-6 alpha-D-glucopyranose 
• 50-99-7 D-glucose 
• 4205-23-6 D-gulose 
• 4613-62-1 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 582-52-5 1,2:5,6-diacetone-D-glucose 

Downstream Products

• 55652-03-4 O¹,O²;O⁵,O⁶-diisopropylidene-3-((E)-5-oxo-2-phenyl-oxazol-4-ylidene)-α-D-ribo-3-deoxy-hexofuranose 
• 77312-87-9 2-[(3aR,5S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-1-(3-nitro-phenyl)-ethanone 
• 77312-86-8 1-(4-Bromo-phenyl)-2-[(3aR,5S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-ethanone 
• 59861-91-5 desoxy-3-di-O-isopropylidene-1,2:5,6-α-D-ribo-hexofurannose-3-spiro-2'-benzimidazoline 
• 142433-30-5 (Z)-3-deoxy-2-phenylhydrazono-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose 
• 142433-31-6 (E)-3-deoxy-2-phenylhydrazono-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose 
• 77312-85-7 1-(4-Chloro-phenyl)-2-[(3aR,5S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-ethanone 
• 77326-01-3 2-[(3aR,5S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6Z)-ylidene]-1-(4-methoxy-phenyl)-ethanone 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 10578-85-5 1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranos-3-ulose hydrate 
• 189456-74-4 (S)-Dibenzylamino-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetic acid methyl ester 
• 1053616-65-1 2-[(2R,4S,5R)-2-Phenyl-4-((2S,4R,5S)-2-phenyl-5-trityloxymethyl-[1,3]dioxolan-4-yl)-5-trimethylsilanyloxy-[1,3]dioxan-5-yl]-thiazole 
• 2595-05-3 Diacetone D-glucose 
• 14686-88-5 3-O-acetyl-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose 

Relevant academic research and scientific papers

Indirect Electrooxidation by Using Ruthenium Tetraoxide and Chloride Ion as Recycling Mediators. Optimization for the Oxidation of Diisopropylidene-D-glucose to the Ulose

Various Various factors related to the yield and selectivity for the indirect electrooxidation of diidopropylidene-glucose (1) to the ulose 2 with ruthenium tetraoxide (RuO4) and chloride ion are investigated.The following is found to be optimum conditions: pH, ca. 10:solvent system, carbon tetrachloride and t-butyl alcohol (ca.9:1); current density, 10-40 mAcm2-; temperature, 20-40 deg C; catalyst amount, 2 molpercent of RuO2.2H2O (based on 1).The optimized electrolysis affords the desired 2 in 90 percent yield along with a trace of the cleavaged product 3 (0.2percent) by an overoxidation.

Unprecedented 3-O-methyl-3-C-trifluoromethyl-d-ribono- (and l-lyxono)-γ-lactones synthesized by nucleophilic trifluoromethylation of d-hexose-derived cyclic ketones

3-O-Methyl-3-C-trifluoromethyl-d-ribono-(and l-lyxono)-γ-lactones have been prepared from protected d-hexoses (gluco, galacto) by multi-step routes from d-glucose. The synthetic strategy includes the following steps: regioselective oxidation, nucleophilic trifluoromethylation with the Ruppert-Prakash reagent of 3-keto hexofuranose derivatives attacked stereoselectively from the less hindered face, protective group manipulations, and regioselective oxidation of a hemiacetalic hydroxyl. Base-catalyzed hydrolysis of two related d-ribonolactones afforded 3-O-Me-3-C-CF3-d-ribonic acid.

Synthesis and glycosidase inhibition evaluation of (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol

A new azasugar (3S,4S)-3-((R)-1,2-dihydroxyethyl)pyrrolidine-3,4-diol (1) was obtained from commercially available D-glucose using one-pot reductive cyclization as a key step. The target product, i.e., the iminosugar isomer, was obtained in 10 steps and 24.3% overall yield. Only three column chromatography purifications were needed in this synthesis. The biological activity of the target molecule as glycosidase inhibitor was studied, but the inhibitory activity against four glycosidases was not good (IC50?>?100?μM).

Sequential Enyne-Metathesis/Diels–Alder Strategy: Rapid Access to Sugar–Oxasteroid–Quinone Hybrids

A sequential enyne-metathesis/Diels–Alder strategy is reported for the synthesis of a new class of sugar–oxasteroid–quinone hybrid molecules. 1,2:5,6-Di-O-isopropylidine-d-glucose was chosen as a chiral-pool starting material. Various sugar-derived enynes were synthesised from the common starting material. Dienes derived from these enynes were treated with various quinone dienophiles under Diels–Alder reaction conditions to give a library of sugar–oxasteroid–quinone hybrids.

Easy and stereoselective approach to α,β-unsaturated γ-lactones fused to pyranoses from furanose scaffolds

The first facile and efficient route to pyranose-fused butenolides from furanose scaffolds, convenient for scaling up production, is described. Wittig olefination of 1,2-O-isopropylidene pentofuranos- or hexofuranos-3-uloses with a resonance-stabilized yl

Synthesis and Evaluation of 2′-Deoxy-2′-Spirodiflurocyclopropyl Nucleoside Analogs

The preparation of 2′-deoxy-2′-siprodifluorocyclopropany-lnucleoside analogs has been achieved from α-d-glucose in several steps. The key step in the synthesis was the introduction of the difluorocyclopropane through a difluorocarbene type reaction at the 2′-position. Then, a series of novel 2′-deoxy-2′-spirodifluorocyclopropanyl nucleoside analogs were synthesized using the Vorbrüggen method. All the synthesized nucleosides were characterized and subsequently evaluated against hepatitis C and influenza A virus strains in vitro.

Branched-chain functionalised carbohydrates via β-functionalised organolithium compounds

The reaction of the epoxysugar 1 with an excess of lithium powder and a catalytic amount of DTBB (5 mol%) in THF at -78°C leads to the formation of the corresponding β-oxido functionalised organolithium intermediates 2, which by treatment with different electrophiles [H2O, D2O, Me3SiCl, PhCHO, Me2CO, (CH2)5CO] at -78°C to room temperature afford, after hydrolysis with water, the expected enantiomerically pure compounds 3. Starting from the epimeric epoxide 4 and following the same procedure, using water as electrophile, the compound 6 was isolated, the corresponding intermediate 5 having been involved in the process.

Chemoenzymatic Syntheses of Fluoro Sugar Phosphates and Analogues

Combined chemical and enzymatic procedures are described for the preparation of fluorinated sugar phosphates and analogues.These derivatives are useful for study of sugar metabolism and for synthesis of pharmacological probes in a number of enzymatic systems utilizing sugars.

Enantioselective preparation of 1,3-dithiane 1-oxides by asymmetric oxidation of 1,3-dithianes bearing a chiral auxiliary

Oxidation of 1,3-dithianes bearing a chiral auxiliary derived from (+) or (-)-camphor or diacetone D-(+)-glucose by the Sharpless reagent [Ti(OPi)4-diethyl L-(+)- or D-(-)-tartrate-ButOOH] affords, with high stereoselectivity, the monosulfoxides in good to excellent yields. Removal of the chiral auxiliary by base-catalysed hydrolysis yields (R)- and (S)-1,3-dithiane 1-oxides in high yields.

Synthesis of 3-deoxy-3-C-trifluoromethyl-D-ribose from D-xylose or D-glucose

The synthesis of 3-deoxy-1,2-O-isopropylidene-3-C-trifluoromethyl-α-D-ribofuranose is described. After a first approach from a commercial D-xylose derivative which was limited by an incomplete stereoselectivity, the synthesis of the title compound was performed from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose by a reaction sequence where key steps: trifluoromethylation with CF3SiMe3 and radical deoxygenation are highly stereoselective.