CAS No.2595-05-3,1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	2595-05-3
Name:	1,2:5,6-Di-O-isopropylidene-Alpha-D-Allofuranose
Article Data:	76

Formula:	C₇H₉N₃O₂
Molecular Weight:	260.287
Synonyms:	Allofuranose, 1,2:5,6-di-O-isopropylidene-, a-D-(7CI,8CI);1,2:5,6-Di-O-isopropylidene-a-D-allofuranose;1,2:5,6-Diacetone-D-allofuranose;Diacetone-D-allofuranose;(3aR,5S,6R,6aR)-5-[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (non-preferred name);
Density:	1.214 g/cm³
Melting Point:	73-77oC
Boiling Point:	362.753 °C at 760 mmHg
Flash Point:	173.187 °C
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	22-24/25-36/37-26
PSA:	66.38000
LogP:	0.37520

Synthetic route

: 2,2,2-Trichloro-acetimidic acid (3aR,5R,6R,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

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol for 2h; Ambient temperature;	100%

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0 - 20℃; for 2h;	96%
With sodium tetrahydroborate In ethanol; water at 0℃; for 1h;	90%
With sodium tetrahydroborate In ethanol; water at 20℃; for 3h; stereoselective reaction;	84%

: 226943-46-0
3-O-tetrahydropyranyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
With water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetonitrile at 75℃; for 0.5h;	91%
With iodine In methanol at 20℃; for 1h; acetal cleavage;	90%

: 226943-66-4
3-O-(4,4'-dimethoxytrityl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
With iodine In methanol at 20℃; for 1h; ether cleavage;	88%
With water; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate In acetonitrile at 75℃; for 0.25h;	85%

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

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78℃; Stage #2: With sodium tetrahydroborate In methanol at 0℃;	85%
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With dipyridinium dichromate; acetic anhydride In dichloromethane Stage #2: With sodium tetrahydroborate In ethanol	83%
Stage #1: 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride In dichloromethane at -65 - 20℃; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 1h;	82%

: 2847-00-9
1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

A: 2595-05-3
Diacetone D-glucose

B: 582-52-5
1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol	A 4.49 g B n/a

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

C6H6O2(OBn)3(OPiv)SP(S)(OEt)2: C6H6O2(OBn)3(OPiv)SP(S)(OEt)2

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3; Ac2O; pyridine / CH2Cl2 / 1 h / 0 °C 2: 8.0 g / NaBH4 / ethanol / 0.5 h / 0 °C View Scheme
Multi-step reaction with 2 steps 1: CrO3; Ac2O; pyridine / CH2Cl2 / 2.5 h / 0 - 20 °C 2: 4.49 g / NaBH4 / methanol View Scheme
Multi-step reaction with 2 steps 1: 85 percent / PCC; 3 Angstroem molecular sieves; neutral alumina / CH2Cl2 / 15 h / 20 °C 2: 96 percent / NaBH4 / aq. ethanol / 2 h / 0 - 20 °C View Scheme

: 492-62-6
alpha-D-glucopyranose

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 32 percent / ZnCl2; H3PO4 / 30 h / 20 °C 2: 85 percent / PCC; 3 Angstroem molecular sieves; neutral alumina / CH2Cl2 / 15 h / 20 °C 3: 96 percent / NaBH4 / aq. ethanol / 2 h / 0 - 20 °C View Scheme

: 2280-44-6
D-Glucose

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 68 percent / ZnCl2; aq. H3PO4 / 36 h / 20 °C 2: 91 percent / pyridinium dichromate; acetic anhydride / CH2Cl2 / 4 h / 75 °C 3: 90 percent / NaBH4 / ethanol; H2O / 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: phosphoric acid; zinc(II) chloride / 36 h / Reflux 2: dipyridinium dichromate; acetic anhydride / dichloromethane / 2 h 3: sodium tetrahydroborate / ethanol / 2 h View Scheme
Multi-step reaction with 2 steps 1: zinc(II) chloride; phosphoric acid / acetone 2: acetic anhydride; pyridinium chlorochromate / dichloromethane View Scheme
Multi-step reaction with 3 steps 1: zinc(II) chloride; phosphoric acid 2: acetic anhydride; dipyridinium dichromate / dichloromethane 3: sodium tetrahydroborate / ethanol View Scheme
Multi-step reaction with 3 steps 1: sulfuric acid 2: chromium(VI) oxide; pyridine; acetic anhydride / dichloromethane / 0.42 h / Cooling with ice 3: sodium tetrahydroborate; ethanol / Cooling with ice View Scheme

: 4205-23-6
D-gulose

: 2595-05-3
Diacetone D-glucose

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: zinc(II) chloride / Inert atmosphere; Schlenk technique 2: chromium(VI) oxide; acetic anhydride; pyridine / Inert atmosphere; Schlenk technique 3: sodium tetrahydroborate / ethanol; water / 3 h / 0 °C / Inert atmosphere; Schlenk technique View Scheme

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Chemistry

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is called for 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranoside ; Diacetone-alpha-D-all ; 5-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-D][1,3]dioxol-6-ol ; Diisopropylideneallofuranose ; Diacetoneglucose ; ZINC04262105 ; CID7157054 ,and so on. 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is white solid.

IUPAC Name: (3aR,5S,6R,6aR)-5-[(4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
CAS: 2595-05-3
Molecular Formula: C₁₂H₂₀O₆
Molecular Weight: 260.28
Molecular structure:
Melting point: 73-76 °C(lit.)
Storage temp.: 2-8°C
H bond acceptors: 6
H bond donors: 1
Freely Rotating Bonds: 2
Index of Refraction: 1.483
Molar Refractivity: 61.24 cm³
Molar Volume: 214.3 cm³
Polarizability: 24.28 10^-24cm³
Surface Tension: 43.6 dyne/cm
Density: 1.214 g/cm³
Flash Point: 173.2 °C
Enthalpy of Vaporization: 70.46 kJ/mol
Boiling Point: 362.8 °C at 760 mmHg
Vapour Pressure: 9.94E-07 mmHg at 25°C

Uses

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) is commonly used as chemical reagent.

Safety Profile

Hazard Codes: Xi
Risk Statements: 36/37/38 (36/37/38: Irritating to eyes, respiratory system and skin)
Safety Statements: 22-24/25-36/37-26 (22: Do not breathe dust 24/25: Avoid contact with skin and eyes 36/37: Wear suitable protective clothing and gloves 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice)
WGK Germany: 3
F: 21

Specification

Removal in wastewater treatment of 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose (2595-05-3) can be stated as follows:
Total removal:2.71 percent
Total biodegradation:0.10 percent
Total sludge adsorption:2.62 percent
Total to Air:0.00 percent
(using 10000 hr Bio P,A,S)