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582-52-5

Basic Information
CAS No.: 582-52-5
Name: a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-
Article Data: 36
Cas Database
Molecular Structure:
Molecular Structure of 582-52-5 (a-D-Glucofuranose,1,2:5,6-bis-O-(1-methylethylidene)-)
Formula: C12H20O6
Molecular Weight: 260.287
Synonyms: Glucofuranose,1,2:5,6-di-O-isopropylidene-, a-D- (6CI,7CI,8CI);(-)-1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose;1,2:5,6-Di-O-isopropylidene-D-glucofuranose;1,2:5,6-Di-O-isopropylidene-D-glucose;1,2:5,6-Di-O-isopropylidene-a-D-glucofuranose;1,2:5,6-Di-O-isopropylidene-a-D-glucose;1,2:5,6-Diisopropylidene-a-D-glucofuranose;D-Glucose diacetonide;Diacetone glucose;Diacetone-D-glucose;Glucosebisacetonide;Glucose diacetonide;NSC 1223;
EINECS: 209-486-0
Density: 1.214 g/cm3
Melting Point: 110-111 °C(lit.)
Boiling Point: 362.8 °C at 760 mmHg
Flash Point: 173.2 °C
Solubility: slightly soluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36/37-26
Transport Information: N/A
PSA: 66.38000
LogP: 0.37520
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

(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

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
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%
153763-40-7

3-O-allyloxycarbonyl-1,2,5,6-di-O-isopropylidene-α-D-glucofuranose

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
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%
428500-97-4

3-O-(2-azidomethyl)phenylacetyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

A

24331-94-0

1,4-dihydro-3(2H)-isoquinolinone

B

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
With hydrogen; Lindlar's catalyst In methanol at 20℃; for 3h;A n/a
B 100%
18685-18-2

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
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

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); p-toluene sulfinic acid In dichloromethane for 0.5h; Ambient temperature;98%
16713-80-7

3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
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;
2280-44-6

D-Glucose

67-64-1

acetone

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
With iodine96%
With phosphoric acid; zinc(II) chloride93%
vanadyl triflate In acetonitrile at 20℃; for 10h;89%
753488-63-0

1,2:5,6-di-O-isopropylidene-3-O-methylprenyl-α-D-glucofuranose

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
With (PhSO2)2; water In dichloromethane at 80℃;96%
50-99-7

D-glucose

67-64-1

acetone

582-52-5

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions
ConditionsYield
With phosphoric acid; zinc(II) chloride95%
With phosphoric acid; zinc(II) chloride for 30h; Ambient temperature;91%
With sulfuric acid Inert atmosphere;85%
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Chemistry

IUPAC Name: 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol 
Following is the structure of Diacetone-D-glucose (CAS NO.582-52-5):
                                
Empirical Formula: C12H20O6
Molecular Weight: 260.2836
EINECS: 209-486-0
Index of Refraction: 1.483
Molar Refractivity: 61.24 cm3
Molar Volume: 214.3 cm3
Density: 1.214 g/cm3
Flash Point: 173.2 °C
Surface Tension: 43.6 dyne/cm
Enthalpy of Vaporization: 70.46 kJ/mol
Boiling Point: 362.8 °C at 760 mmHg
Water Solubility: slightly soluble
Storage temp.: −20 °C
Vapour Pressure: 9.94E-07 mmHg at 25 °C
Appearance of Diacetone-D-glucose (CAS NO.582-52-5): white to light yellow crystal powde
Product Categories of Diacetone-D-glucose (CAS NO.582-52-5): Pharmaceutical Intermediates; Sugars, Carbohydrates & Glucosides; chiral; Biochemistry; Glucose; O-Substituted Sugars; Sugars; Carbohydrates & Derivatives; Carbohydrates
Canonical SMILES: CC1(OCC(O1)C2C(C3C(O2)OC(O3)(C)C)O)C
InChI: InChI=1S/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
InChIKey: KEJGAYKWRDILTF-UHFFFAOYSA-N

Toxicity Data With Reference

1.    

orl-mus LD50:4 g/kg

    ARZNAD    Arzneimittel-Forschung. Drug Research. 29 (1979),986.

 Diacetone-D-glucose (CAS NO.582-52-5) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated. You can see actual entry in RTECS for complete information.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Mildly toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 24/25-36/37-26 
S24/25:Avoid contact with skin and eyes. 
S36/37:Wear suitable protective clothing and gloves. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS: LZ4958000
F: 3-10
HS Code: 29329970

Specification

 Diacetone-D-glucose , its cas register number is 582-52-5. It also can be called 1,2:5,6-Diisopropylidene-D-glucose ; 1,2,5,6-Diisopropylidene-D-glucose ; D-Glucose diacetonide ; and Diacetone glucose . Its classification code is Drug / Therapeutic Agent. 
 Tri-p-tolyl phosphite (CAS NO.63845-31-8) could be stable under normal temperatures and pressures. It should avoid the condition like incompatible materials. It is not compatible with strong oxidizing agents. And also prevent it to broken down into hazardous decomposition products: carbon monoxide, carbon dioxide. However, its hazardous polymerization has not been reported.

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