2847-00-9

Basic information

• Product Name: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSE
• Synonyms: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSULOSE;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSE;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSULOSE;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-HEXOFURANOSE-3-ULOSE;1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBOHEXULOFURANOS-3-ULOSE;1,2:5,6-DI-O-ISOPROPYLIDENE-A-D-RIBO-HEXOFURANOSE-3-ULOSE;1,2:5,6-DI-O-ISOPROPYLIDINE-ALPHA-D-RIBO-HEXULOFURANOS-3-ULOSE
• CAS NO: 2847-00-9
• Molecular Formula: C₁₂H₁₈O₆
• Molecular Weight: 258.27
• EINECS: 220-646-9
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 2847-00-9.mol
• Article Data: 162

Chemical Properties

• Melting Point: 65-70°C
• Boiling Point: 361.52°C (rough estimate)
• Flash Point: 165.4 °C
• Appearance: colorless very viscous liquid
• Density: 1.2675 (rough estimate)
• Vapor Pressure: 0.000152mmHg at 25°C
• Refractive Index: 1.5230 (estimate)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSE(2847-00-9)
• EPA Substance Registry System: 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXULOFURANOSE(2847-00-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 2847-00-9(Hazardous Substances Data)

Usage

Description

1,2:5,6-Di-O-isopropylidene-alpha-D-ribo-3-hexulofuranose is a colorless, very viscous liquid that is a mixture of keto and ketal forms. It is a compound with the CAS number 2847-00-9 and is useful in organic synthesis.

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 
• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-D-glucofuranoside 
• 4205-23-6 D-gulose 

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 
• 96212-44-1 (3aR,5R,6R,6aR)-6-Benzyloxy-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 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 

Relevant articles and documents

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.

Mechanistic studies of the biosynthesis of 3,6-dideoxy sugars: Stereochemical analysis of C-3 deoxygenation

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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).

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

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.

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.

Synthesis and analysis of a fluorinated product analogue as an inhibitor for 1-deoxy-d-xylulose 5-phosphate reductoisomerase

1-Deoxy-d-xylulose 5-phosphate (DXP) reductoisomerase (DXR) is an NADPH-dependent enzyme catalyzing the rearrangement and reduction of DXP to methyl-d-erythritol 4-phosphate (MEP). Two mechanisms for this enzymatic reaction have been proposed, involving either an α-ketol rearrangement or a retroaldol/aldol rearrangement. In this study, a fluorinated product analogue, FCH2-MEP, was synthesized as a possible mechanism-based inactivator for DXR if the retroaldol/aldol mechanism is operative. FCH2-MEP was found to be a weak competitive inhibitor, and thus was unable to discriminate between the mechanisms. This result is due to the inability of the targeted enzyme, DXR, to oxidize FCH2-MEP to the aldehyde intermediate that is common to both mechanisms. While FCH2-MEP failed to act as a mechanism-based inactivator, the insight gained from this study will assist in the future design of inhibitors of DXR.

Correlating Hydration Shell Structure with Amino Acid Hydrophobicity

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Molar-scale synthesis of 1,2:5,6-Di-0-isopropylidene-α-D- allofuranose: DMSO oxidation of 1,2:5,6-Di-0-isopropylidene-α-D- glucofuranose and subsequent sodium borohydride reduction

Two variants of oxidation with DMSO followed by sodium borohydride reduction have been investigated to make the synthesis of 1,2:5,6-di-0- isopropylidene-α-D-allofuranose (4) suitable for large-scale manufacturing.

Synthesis method of 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose

The invention provides a synthesis method of 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose. The synthesis method comprises the following steps: reacting glucose with acetone to obtain a first intermediate product; carrying out oxidation reaction on the first intermediate product through N-bromosuccinimide to obtain a second intermediate product; carrying out reduction reaction on the second intermediate product through sodium borohydride to obtain a third intermediate product; reacting benzyl chloride with the third intermediate product to obtain a fourth intermediate product; reacting the fourth intermediate product with an acidic solution to obtain a fifth intermediate product; and carrying out oxidation reaction and disproportionation reaction on the fifth intermediate product to obtain the 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose. The 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-alpha-D-ribofuranose is synthesized by taking the glucose with low price as a raw material through six steps.

PRMT5 INHIBITORS

The present invention provides a compound of Formula (I) and the pharmaceutically acceptable salts, esters, and prodrugs thereof, which are PRMT5 inhibitors. Also provided are methods of making compounds of Formula I, pharmaceutical compositions comprising compounds of Formula I, and methods of using these compounds to treat cancer, sickle cell, and hereditary persistence of foetal hemoglobin (HPFH) mutations.