1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose

ChemicalBook > CAS DataBase List > 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose

Synthesis

Product Name: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose
CAS No.: 2595-05-3
Chemical Name: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose
Synonyms: 1,2:5,6-DI-O-ISOPROPYLIDENE-A-D-ALLOFURANOSE;(3aR,5S,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol;Diacetone-D-allofuranose;2595-05-3-;1,2:5,6-Di-O-isoprop;DIACETONE-ALPHA-D-ALL;Diisopropylideneallofuranose;1,2:5,6-Diacetone-D-allofuranose;1,2:5,6-Di-O-isopropylidene-alpha-D-allo;5,6-Di-O-isopropylidene-a-D-allofuranose
CBNumber: CB1128376
Molecular Formula: C12H20O6
Formula Weight: 260.28
MOL File: 2595-05-3.mol

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1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose Property

Melting point:: 73-76 °C(lit.)
alpha: 37.5 º (c=1,chloroform)
Boiling point:: 363.54°C (rough estimate)
Density: 1.2377 (rough estimate)
refractive index: 36.5 ° (C=1, CHCl3)
storage temp.: Inert atmosphere,Store in freezer, under -20°C
solubility: almost transparency in Toluene
pka: 13.15±0.60(Predicted)
form: Powder
color: White to off-white
Stability:: Acid Sensitive
InChIKey: KEJGAYKWRDILTF-BHRXDNSCSA-N
CAS DataBase Reference: 2595-05-3(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 22-24/25-36/37-26
WGK Germany: 3
F: 21
HS Code: 29400090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H226Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 296376
Product name: 1,2:5,6-Di-O-isopropylidene-α-D-allofuranose
Purity: 98%
Packaging: 1g
Price: $30
Updated: 2023/01/07

TCI Chemical

Product number: D2265
Product name: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose
Purity: >98.0%(GC)
Packaging: 1g
Price: $55
Updated: 2024/03/01

TCI Chemical

Product number: D2265
Product name: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose
Purity: >98.0%(GC)
Packaging: 5g
Price: $163
Updated: 2024/03/01

Alfa Aesar

Product number: J66388
Product name: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose, 98%
Packaging: 1g
Price: $62.65
Updated: 2024/03/01

Alfa Aesar

Product number: J66388
Product name: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose, 98%
Packaging: 5g
Price: $191
Updated: 2021/12/16

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1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose Chemical Properties,Usage,Production

Synthesis

Anhydrous DMSO (650 mL) was cooled to 18−20 °C under nitrogen in a 3-L roundbottomed glass flflask. DMSO solidififies at 18 °C and therefore it is important to keep the reaction mixture just above freezing point. To this cold solution was added P2O5 (142 g, 1.0 mol, 1 equivalent) in 3 portions under a N2 atmosphere. The addition of P2O5 to DMSO is exothermic, and if the mass temperature exceeds 28 °C, the color darkens and the product will be of inferior quality. The mixture was cooled to 18−20 °C between each addition. After addition of P2O5 was completed, the mixture was stirred at 18−25 °C for 10−15 min. 1,2:5,6-Di-O-isopropylidene-D-glucofuranose (260 g, 1.0 mol) was dissolved in anhydrous DMSO (1.3 L) and added over 30 min (maintaining the temperature at 18−25 °C) to the stirred solution of P2O5 in DMSO under a N2 atmosphere. The resulting solution was heated to 50−55 °C for 3 h. TLC (eluent: CH2Cl2:MeOH, 95:5) shows complete conversion of glucofuranose (Rf = 0.68) to ulose (Rf = 0.81). The reaction mixture was allowed to reach 25−30 °C and was extracted twice with methyl tert-butyl ether (MTBE 1.5 and 1 L) in a 6-L separation funnel. The combined MTBE layer (~4 L) was concentrated in vacuo (water-bath temperature set to 40 °C) to approximately 2 L and allowed to reach 25−30 °C. NaBH4 (24 g, 0.63 mol) was dissolved in water (1 L, 55.6 mol) at 0−10 °C, and the concentrated MTBE layer was added to the aqueous layer over 30 min to keep the temperature at 0−10 °C. TLC (eluent: EtOAc/heptane, 6:4) after 30 min shows full conversion of ulose (Rf = 0.53) to 1,2:5,6-di-O-isopropylidene-D-allofuranose (Rf = 0.39). The reaction mixture was allowed to reach 25−30 °C. CH2Cl2 (1 L) and water (500 mL) were added, and the layers were separated. The aqueous layer was extracted once more with CH2Cl2 (500 mL). The combined organic layers were concentrated in vacuo to an oil which was subsequently dissolved in MTBE (300 mL) and extracted with water (3 × 500 mL). The combined aqueous layers were extracted with CH2Cl2 (3 × 500 mL). The combined CH2Cl2 layers were dried (Na2SO4, 100 g), fifiltered, and concentrated in vacuo to provide the crude oil. Crystallization from cyclohexane (500 mL), washing of crystals with cold n-pentane, and drying hereof in vacuo afforded analytically pure 1,2:5,6-di-O-isopropylidene-D-allofuranose (191 g, 73%).

Reference: Christensen, S. M.; Hansen, H. F.; Koch, T. Org. Proc. Res. Dev. 2004, 8, 777−780.

Chemical Properties

White Solid

Uses

Protected α-D-Allofuranose

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose manufacturers

Henan Fengda Chemical Co., Ltd

Product: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose 2595-05-3
Price: US $6.00-0.60/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: g-kg-tons, free sample is available
Release date: 2024-03-22

Hebei Mojin Biotechnology Co., Ltd

Product: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose 2595-05-3
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-08-31

Hebei Guanlang Biotechnology Co., Ltd.

Product: 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose 2595-05-3
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2021-09-01

2595-05-3, 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranoseRelated Search:

Azlocillin sodium Diacetone-D-glucose Azlocillin ALOSETRON D-(+)-ALLOSE 3-O-BENZYL-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE 1,2:5,6-DI-O-CYCLOHEXYLIDENE-3-O-METHYLSULFONYL-ALPHA-D-ALLOFURANOSE 1,2:5,6-DI-O-CYCLOHEXYLIDENE-3-CYANO-ALPHA-D-ALLOFURANOSE 1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-RIBO-3-HEXOFURANOSE-3-ULOSE MONOHYDRATE 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose

1,2:5,6-Di-O-isopropylidene-alpha-D-allo

1,2:5,6-Di-O-isoprop

1,2:5,6-Di-O-isopropylidene-α-D-allofuranose ,98%

1,2:5,6-Bis-O-(1-Methylethylidene)-α-D-allofuranose

1,2:5,6-Diacetone-D-allofuranose

Diacetone-D-allofuranose

1,2:5,6-Di-O-isopropylidene-alpha-D-ribo-hexofuranose

1,2:5,6-bis-O-(1-Methylethylidene)-alpha-D-Allofuranose

2:5,6-Di-O-isopropylidene-alpha-D-allofuranose

1,2:5,6-Di-O-isopropylidene-a-D-allofuranose, Diacetone-D-allofuranose

1,2:5,6-DI-O-ISOPROPYLIDENE-D-ALLOFURANOSE

1,2:5,6-DI-O-ISOPROPYLIDENE-A-D-ALLOFURANOSE

1,2,5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE

1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE

1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSIDE

DIACETONE-ALPHA-D-ALL

1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSIDE 98%

5-(2,2-DIMETHYL-[1,3]DIOXOLAN-4-YL)-2,2-DIMETHYL-TETRAHYDRO-FURO[2,3-D][1,3]DIOXOL-6-OL

Diisopropylideneallofuranose

1-O,2-O:5-O,6-O-Bis(1-methylethylidene)-α-D-allofuranose

1-O,2-O:5-O,6-O-Diisopropylidene-α-D-allofuranose

1-O,2-O:5-O,6-O-Diisopropylidene-α-D-allo-hexofuranose

1-O,2-O-Isopropylidene-5-O,6-O-isopropylidene-α-D-allofuranose

1,2:5,6-Di-O-isopropylidene-alpha-D-allo-furanose,98%

5,6-Di-O-isopropylidene-a-D-allofuranose

(3aR,5S,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

(3aR,5S,6R,6aR)-5-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,2-d][1,3]dioxol-6-ol

(3aR,5S,6R,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

5,6-Di-O-isopropylidene-alpha-D-allofuranose

1,2:5,6-Di-O-isopropylidene-α-D-allofuranose&gt

α-D-Allofuranose, 1,2:5,6-bis-O-(1-methylethylidene)-

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose USP/EP/BP

(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

2595-05-3-

1,2:5,6-Bis-O-(1-methylethylidene)-α-D-allofuranose

2595-05-3

2595/5/3

253968

2905-05-3

2595-5-3

2595-06-3

253-96-8

2595-05-34

5/3/2595

2595-03-5

Monosaccharides

Specialty Synthesis

O-Substituted Sugars

Allose

Sugars

Carbohydrate Synthesis

13C & 2H Sugars

Allose

Biochemistry

O-Substituted Sugars

Sugars

Carbohydrates & Derivatives

Carbohydrate Synthesis