14686-89-6

Basic information

• Product Name: DIACETONE-D-GLUCOSE
• Synonyms: GLUCOFURANOSE;DIISOPROPYLIDENEGLUCOFURANOSE;DI-O-ISOPROPYLIDENE-A-D-GLUCOFURANOSE, 1,2,5,6-;DIACETONE-ALPHA-D-GLC;DIACETONE-ALPHA-D-GLUCOSE;1,2:5,6-O-DI-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSIDE;1,2:5,6-DIISOPROPYLENE-ALPHA-D-GLUCOFURANOSE;(-)-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
• CAS NO: 14686-89-6
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• EINECS: 209-486-0
• Product Categories: Carbohydrates & Derivatives
• Mol File: 14686-89-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 110-111 °C(lit.)
• Boiling Point: 362.8 °C at 760 mmHg
• Flash Point: 173.2 °C
• Appearance: Off-white crystalline solid
• Density: 1.214 g/cm³
• Vapor Pressure: 9.94E-07mmHg at 25°C
• Refractive Index: 1.483
• Storage Temp.: −20°C
• PKA: 13.15±0.60(Predicted)
• CAS DataBase Reference: DIACETONE-D-GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: DIACETONE-D-GLUCOSE(14686-89-6)
• EPA Substance Registry System: DIACETONE-D-GLUCOSE(14686-89-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 2
• RTECS: LZ4958000
• F: 3-10
• Hazardous Substances Data: 14686-89-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Crystalline Solid

Uses

1,2:5,6-Di-O-isopropylidene-α-D-gulofuranose was a useful reagent in the preparation of fluorinated UDP-galactofuranose probes.

InChI:InChI=1/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6-,7+,8-,9-,10-/m1/s1

Upstream product

• 921-60-8 L-glucose 
• 67-64-1 acetone 
• 121701-18-6 1,2-O-isopropylidene-α-L-glucofuranose 
• 1990-29-0 D-altrose 
• 29586-98-9 3-O-acetyl-1,2,5,6-di-isopropylidene-α-D-glucofuranose 
• 582-52-5 1,2:5,6-Di-O-isopropylidene-β-D-altrofuranose 
• 41846-94-0 D-altrose 
• 26623-16-5 1,2:5,6-di-O-isopropylidene-β-D-arabino-hexofuranos-3-ulose 
• 59401-65-9 1,2:5,6-Di-O-Isopropyliden-3-O-pentaflyl-α-D-allofuranose 
• 116408-84-5 2,2,2-Trifluoro-1,1-diphenyl-ethanesulfonic acid (3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 16713-80-7 Acetic acid (3aR,5S,6R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 50-99-7 D-glucose 
• 77-76-9 2,2-dimethoxy-propane 
• 6027-42-5 (2S,3S,4S)-6-Nitro-hexane-1,2,3,4,5-pentaol 

Downstream Products

• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 59401-65-9 1,2:5,6-Di-O-Isopropyliden-3-O-pentaflyl-α-D-allofuranose 
• 199458-13-4 1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-3-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione 
• 171762-97-3 1-[(2R,3R,4R,5R)-5-((S)-1-Azido-ethyl)-4-benzyloxy-3-methoxy-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione 
• 171762-98-4 1-[(2R,3R,4R,5R)-5-((S)-1-Amino-ethyl)-4-benzyloxy-3-methoxy-tetrahydro-furan-2-yl]-3-(4-methoxy-benzyloxymethyl)-5-methyl-1H-pyrimidine-2,4-dione 
• 199458-24-7 Toluene-4-sulfonic acid (R)-2-hydroxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester 
• 199458-26-9 Toluene-4-sulfonic acid (R)-1-[(3aR,5S,6R,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethyl ester 
• 199458-29-2 Acetic acid (3R,4R,5R)-2-acetoxy-5-((S)-1-azido-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-3-yl ester 
• 171762-91-7 Toluene-4-sulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl ester 
• 171762-93-9 Acetic acid (3R,4R,5R)-2-acetoxy-5-((S)-1-azido-ethyl)-4-benzyloxy-tetrahydro-furan-3-yl ester 
• 199458-27-0 (3aR,5R,6R,6aR)-5-((S)-1-Azido-ethyl)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 199458-25-8 (R)-1-[(3aR,5R,6R,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-ethanol 
• 70632-45-0 (R)-1-((3aR,5R,6R,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethanol 
• 117257-22-4 3-O-benzyl-1,2-O-isopropylidene-6-O-p-toluenesulfonic-α-D-allofuranose 

Relevant articles and documents

Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides

A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is

Larger laboratory scale synthesis of 5-methyluridine and formal synthesis of its L-enantiomer

A larger laboratory scale synthesis (>60 g per run) of 5-methyluridine is presented. The critical intermediate 1,2-O-isopropylidene-α-D-ribofuranose was prepared from very cheap D-glucose via D-allose. Its L-enantiomer was obtained from L-arabinose via L-glucose, and also from L-xylose. {figure presented}.

Synthesis of a MUC1-glycopeptide-BSA conjugate vaccine bearing the 3′-deoxy-3′-fluoro-Thomsen-Friedenreich antigen

A novel MUC1-glycopeptide-BSA conjugate vaccine with a specifically fluorinated Thomsen-Friedenreich antigen side chain at Thr6 was prepared. Preliminary immunological experiments reveal specific binding of the tumor-associated glycopeptide antigen analog by anti-MUC1-mouse antibodies.