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
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)
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
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.
N-Bromosuccinimide Price
- 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
- 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
- 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
- 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
- Product number
- J66388
- Product name
- 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose, 98%
- Packaging
- 5g
- Price
- $191
- Updated
- 2021/12/16
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
1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose Suppliers
- Tel
- 25-25-58740604 15951658055
- Fax
- +86-25-58356858
- sales@unisyn.cn
- Country
- China
- ProdList
- 537
- Advantage
- 58
- Tel
- 0552-3068102 13966060073
- Fax
- 0552-3068843
- sales@nakochem.com
- Country
- China
- ProdList
- 26
- Advantage
- 58
- Tel
- 0551-68936860-8515 15357955825
- Fax
- 0551-68936860
- 15357955825@163.com
- Country
- China
- ProdList
- 81
- Advantage
- 55
- Tel
- 18795782766
- 769011731@qq.com
- Country
- China
- ProdList
- 29
- Advantage
- 58
- Tel
- 0515-82159088 13770142076
- Fax
- 86-0515-8215909
- twl@njuchem.com
- Country
- China
- ProdList
- 205
- Advantage
- 65
- Tel
- 010-82848833 400-666-7788
- Fax
- 86-10-82849933
- jkinfo@jkchemical.com
- Country
- China
- ProdList
- 96815
- Advantage
- 76
- Tel
- 4006608290; 18621169109
- Fax
- 86-21-61259102
- market03@meryer.com
- Country
- China
- ProdList
- 40241
- Advantage
- 62
- Tel
- 821-50328103-801 18930552037
- Fax
- 86-21-50328109
- 3bsc@sina.com
- Country
- China
- ProdList
- 15848
- Advantage
- 69
- Tel
- 021-67121386
- Fax
- 021-67121385
- Sales-CN@TCIchemicals.com
- Country
- China
- ProdList
- 24539
- Advantage
- 81
- Tel
- 021-021-58432009 400-005-6266
- Fax
- 021-58436166
- sales8178@energy-chemical.com
- Country
- China
- ProdList
- 44751
- Advantage
- 61
View Lastest Price from 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose manufacturers
- 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
- 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
- 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