Synthesis
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
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.

P501Dispose of contents/container to..…

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

Nanjing Baifuli Technology Co., Ltd.
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25-25-58740604 15951658055
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+86-25-58356858
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sales@unisyn.cn
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China
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Bengbu Nako Chemical Co., Ltd.
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0552-3068102 13966060073
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0552-3068843
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sales@nakochem.com
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China
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Anhui Enbang Biological Technology Co., Ltd.
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0551-68936860-8515 15357955825
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0551-68936860
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15357955825@163.com
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China
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Nantong Jiaxingtai Biotechnology Co., Ltd.
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18795782766
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769011731@qq.com
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China
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J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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86-10-82849933
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jkinfo@jkchemical.com
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021-61259108 18621169109
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TCI (Shanghai) Development Co., Ltd.
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021-67121386
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021-67121385
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Energy Chemical
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View Lastest Price from 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose manufacturers

Hebei Weibang 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
2024-10-25
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

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