582-52-5

Basic information

• Product Name: Diacetone-D-glucose
• Synonyms: DIACETONE-D-GLUCOSE;DIACETONEGLUCOSE;DIACETONE-ALPHA-D-GLUCOSE;DIACETONE-ALPHA-D-GLC;D-GLUCOSE DIACETONIDE;DIISOPROPYLIDENEGLUCOFURANOSE;DI-O-ISOPROPYLIDENE-A-D-GLUCOFURANOSE, 1,2,5,6-;GLUCOFURANOSE
• CAS NO: 582-52-5
• Molecular Formula: C₁₂H₂₀O₆
• Molecular Weight: 260.28
• EINECS: 209-486-0
• Product Categories: Pharmaceutical Intermediates;Sugars, Carbohydrates & Glucosides;chiral;Biochemistry;Glucose;O-Substituted Sugars;Sugars;Carbohydrates & Derivatives;Carbohydrates;Non-natural amino acids
• Mol File: 582-52-5.mol

Chemical Properties

• Melting Point: 110-111 °C(lit.)
• Boiling Point: 323.54°C (rough estimate)
• Flash Point: 173.2 °C
• Appearance: White to yellow/Powder
• Density: 1.1432 (rough estimate)
• Vapor Pressure: 9.94E-07mmHg at 25°C
• Refractive Index: -18.5 ° (C=5, H2O)
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water (Slightly, Sonicated)
• PKA: 13.15±0.60(Predicted)
• Water Solubility: slightly soluble
• Merck: 14,2965
• BRN: 84386
• CAS DataBase Reference: Diacetone-D-glucose(CAS DataBase Reference)
• NIST Chemistry Reference: Diacetone-D-glucose(582-52-5)
• EPA Substance Registry System: Diacetone-D-glucose(582-52-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 2
• RTECS: LZ4958000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 582-52-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Used in Biochemical Research:
In the field of biochemical research, Diacetone-D-glucose is utilized as a key compound in various reactions, contributing to the understanding of complex biological processes and the development of novel bioactive molecules.
Used in Organic Synthesis:
1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose, a compound derived from Diacetone-D-glucose, is useful in organic synthesis. It serves as a building block for the creation of more complex organic molecules, which can be applied in various industries, such as pharmaceuticals, agrochemicals, and materials science.

Purification Methods

Diacetone-D-glucose crystallises from Et2O, (needles), pet ether or *C6H6 and sublimes in vacuo. It is soluble in 7 volumes of H2O and 200 volumes of pet ether at their boiling points. The solubility in H2O at 17.5o is 4.3%. It precipitates from aqueous solutions on basification with NaOH. [Schmid & Karrer Helv Chim Acta 32 1371 1949, Fischer & Rund Chem Ber 49 90, 93 1916, IR: Kuhn Anal Chem 22 276 1950, Beilstein 19/12 V 318.]

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

Synthetic route

(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 → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In methanol at 40℃;	100%
With tetrakis(triphenylphosphine) palladium(0); p-toluene sulfinic acid In dichloromethane for 0.416667h; Ambient temperature;	99%
With 1,3-dimethylbarbituric acid; Pd(PPh3) In tetrahydrofuran at 90℃; for 24h;	99%

3-O-allyloxycarbonyl-1,2,5,6-di-O-isopropylidene-α-D-glucofuranose (153763-40-7) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With aminomethyl resin-supported N-propylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃;	100%
With palladium diacetate; sodium azide; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile at 25℃; for 1h;	71%

3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (428500-97-4) → 1,4-dihydro-3(2H)-isoquinolinone (24331-94-0) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With hydrogen; Lindlar's catalyst In methanol at 20℃; for 3h;	A n/a B 100%

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose (18685-18-2) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water for 1h; Sealed tube; Irradiation;	98%
With hydrogen; palladium on activated charcoal In various solvent(s) at 20℃; under 760 Torr; for 10h;	90%
With 3,3-dimethyldioxirane In dichloromethane; acetone for 48h; Ambient temperature;	87.3%

(3aR,5S,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); p-toluene sulfinic acid In dichloromethane for 0.5h; Ambient temperature;	98%

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose (16713-80-7) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With methanol; potassium permanganate; trimethylsulphonium iodide at 25℃; under 760.051 Torr; chemoselective reaction;	96%
acetylesterase from orange peel;	75%
With sodium methylate In tetrahydrofuran for 6h;

D-Glucose (2280-44-6) + acetone (67-64-1) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With iodine	96%
With phosphoric acid; zinc(II) chloride	93%
vanadyl triflate In acetonitrile at 20℃; for 10h;	89%

1,2:5,6-di-O-isopropylidene-3-O-methylprenyl-α-D-glucofuranose (753488-63-0) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With (PhSO2)2; water In dichloromethane at 80℃;	96%

D-glucose (50-99-7) + acetone (67-64-1) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With phosphoric acid; zinc(II) chloride	95%
With phosphoric acid; zinc(II) chloride for 30h; Ambient temperature;	91%
With sulfuric acid Inert atmosphere;	85%

α-D-glucofuranose (610-85-5, 7045-51-4, 19217-07-3, 30412-16-9, 34685-37-5, 36468-79-8, 36468-80-1, 36468-81-2, 36468-82-3, 36468-84-5, 36574-15-9, 36574-18-2, 36574-19-3, 36574-21-7, 36972-23-3, 36978-43-5, 37738-80-0, 40461-75-4, 40461-79-8, 40461-80-1, 40461-83-4, 40550-49-0, 41612-82-2, 41846-85-9, 41846-86-0, 41846-87-1, 41846-88-2, 41846-89-3, 41846-90-6, 41846-91-7, 41846-92-8, 41846-93-9, 41846-94-0, 41846-95-1, 41846-96-2, 41846-97-3, 41847-47-6, 41847-48-7, 41847-49-8, 41847-50-1, 41847-62-5, 41847-63-6, 41847-64-7, 41847-65-8, 41847-66-9, 41847-67-0, 41847-68-1, 51076-04-1, 89673-68-7, 131064-93-2, 131064-94-3, 131064-95-4, 131064-96-5, 131064-97-6, 131065-02-6, 131065-03-7, 131065-04-8, 131065-05-9, 131065-06-0) + acetone (67-64-1) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With diphenylphosphinopolystyrene; iodine at 20℃; for 0.5h;	95%
With sulfuric acid; copper(II) sulfate at 20℃; for 18h;	90%
With sulfuric acid at 5 - 25℃; for 8h;	81.3%
With sulfuric acid at 0℃;
With sulfuric acid

(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodo-nonyloxy)-tetrahydro-furo[2,3-d][1,3]dioxole → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With ammonium chloride; zinc In ethanol for 0.25h; Heating;	93%

1,2:5,6-di-O-isopropylidene-3-O-(3'-methyl-2'-butenyl)-α-D-glucofuranose (224317-43-5) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With (PhSO2)2; water In dichloromethane at 80℃;	93%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane; water at 20℃; for 9h;	65%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dichloromethane for 9h;	65%

1,2:5,6-di-O-isopropylidene-3-O-(2-nitro)phenylacetyl-α-D-glucofuranose (1223405-87-5) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With ammonium chloride; zinc In methanol at 20℃;	93%

C17H32O7SSi → 2-(trimethylsilyl)ethanesulfinamide + (-)-(S)-2-(trimethylsilyl)ethane sulfinamide + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
Stage #1: C17H32O7SSi With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2.2h; Sealed tube; Inert atmosphere; Schlenk technique; Stage #2: With silica gel In methanol at -78 - 23℃; for 1h; Inert atmosphere; Schlenk technique;	A n/a B 65.9% C 92.6%

1,2:5,6-di-O-isopropylidene-3-O-(allenyl)-α-D-glucofuranoside (142363-22-2) → 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5)

Conditions	Yield
With osmium(VIII) oxide; N-methyl-2-indolinone In acetone at 20℃; for 22h; Hydrolysis;	92%

Upstream product

• 50-99-7 D-glucose 
• 67-64-1 acetone 
• 70542-35-7 (3aR,5R,6R,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-nitrooxy-tetrahydro-furo[2,3-d][1,3]dioxole 
• 55951-93-4 1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose 
• 69940-03-0 1,2:5,6-Di-O-isopropyliden-3-O-veratryl-α-D-glucofuranose 
• 16667-96-2 1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 
• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 
• 77-76-9 2,2-dimethoxy-propane 
• 2280-44-6 D-Glucose 
• 536-11-8 D-melibiose 
• 530-26-7 D-Mannose 
• 72045-11-5 2,3:4,6-di-O-isopropylidene-5-thio-α-D-glucopyranose 
• 116-11-0 2-Methoxypropene 
• 112254-61-2 (3aR,4S,5aR,9aS,9bS)-4-(1-Methoxy-1-methyl-ethoxy)-2,2,8,8-tetramethyl-hexahydro-[1,3]dioxolo[4',5':4,5]thiopyrano[3,2-d][1,3]dioxine 

Downstream Products

• 138052-46-7 methyl α,β-D-glucofuranose 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 71978-77-3 3-O-butyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 79378-71-5 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (-)-(S)-p-toluenesulfinate 
• 82079-38-7 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranosyl (+)-(R)-p-toluenesulfinate 
• 64694-21-9 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 64694-22-0 1,2:5,6-di-O-isopropylidene-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-3)-α-D-glucofuranose 
• 22331-28-8 3-O-ethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 91233-25-9 (E)-1-[(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-yloxy]-2-methyl-pent-1-en-3-one 
• 64694-26-4 3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 87735-46-4 3-O-(2-O-benzyl-α-L-fucopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 131791-65-6 Acetic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-[(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-yloxy]-tetrahydro-pyran-2-ylmethyl ester 
• 131791-63-4 3-O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose 
• 124718-69-0 3'-(1',2':5',6'-diisopropyleneglucofuranosyl) 3,4,6-tri-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 

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