ChemicalBook--->CAS DataBase List--->2595-05-3

2595-05-3

2595-05-3 Structure

2595-05-3 Structure
IdentificationMore
[Name]

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

2595-05-3
[Synonyms]

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
1,2:5,6-DI-O-ISOPROPYLIDENE-D-ALLOFURANOSE
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
1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSIDE 98%
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
[Molecular Formula]

C12H20O6
[MDL Number]

MFCD00135634
[Molecular Weight]

260.28
[MOL File]

2595-05-3.mol
Chemical PropertiesBack Directory
[Appearance]

White Solid
[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. ]

2-8°C
[form ]

Powder
[pka]

13.15±0.60(Predicted)
[color ]

White to off-white
[Stability:]

Acid Sensitive
[InChIKey]

KEJGAYKWRDILTF-BHRXDNSCSA-N
[CAS DataBase Reference]

2595-05-3(CAS DataBase Reference)
Questions And AnswerBack Directory
[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%).
Systhesis of 1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose
Reference: Christensen, S. M.; Hansen, H. F.; Koch, T. Org. Proc. Res. Dev. 2004, 8, 777−780.
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S22:Do not breathe dust .
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 ]

3
[F ]

21
[HS Code ]

29400090
Hazard InformationBack Directory
[Chemical Properties]

White Solid
[Uses]

Protected α-D-Allofuranose
Spectrum DetailBack Directory
[Spectrum Detail]

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose(2595-05-3)1HNMR
1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose(2595-05-3)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose, 98%(2595-05-3)
[Sigma Aldrich]

2595-05-3(sigmaaldrich)
[TCI AMERICA]

1,2:5,6-Di-O-isopropylidene-alpha-D-allofuranose,>98.0%(GC)(2595-05-3)
2595-05-3 suppliers list
Company Name: Beijing Ribio Biotech Co.,Ltd
Tel: 010-62664360 +8613328773880 , +8613328773880
Website: http://en.ribio.com.cn/
Company Name: Hebei Mojin Biotechnology Co., Ltd
Tel: +86 13288715578 +8613288715578 , +8613288715578
Website: www.mojinchemical.com
Company Name: Henan Fengda Chemical Co., Ltd
Tel: +86-371-86557731 +86-13613820652 , +86-13613820652
Website: www.fdachem.com
Company Name: Springchem New Material Technology Co.,Limited
Tel: +86-021-62885108 +8613917661608 , +8613917661608
Website: http://www.spring-chem.com/
Company Name: Shanghai Daken Advanced Materials Co.,Ltd
Tel: +86-371-66670886
Website: https://www.dakenchem.com/
Company Name: Shanghai Time Chemicals CO., Ltd.
Tel: +86-021-57951555 +8617317452075 , +8617317452075
Website: www.time-chemicals.com
Company Name: Hangzhou FandaChem Co.,Ltd.
Tel: 008657128800458; +8615858145714 , +8615858145714
Website: http://www.fandachem.com
Company Name: ATK CHEMICAL COMPANY LIMITED
Tel: +undefined-21-51877795
Website: www.atkchemical.com
Company Name: career henan chemical co
Tel: +86-0371-86658258 +8613203830695 , +8613203830695
Website: www.coreychem.com/
Company Name: Jinan Carbotang Biotech Co.,Ltd.
Tel: +8615866703830 , +8615866703830
Website: https://www.chemicalbook.com/ShowSupplierProductsList31189/0.htm
Company Name: Accela ChemBio Inc.
Tel: +1-858-6993322
Website: www.accelachem.com/
Company Name: Yunbio Tech Co.,Ltd.
Tel: +86-010-60605551 +86-18046518538 , +86-18046518538
Website: https://yunbiopharm.com/
Company Name: Hebei Guanlang Biotechnology Co., Ltd.
Tel: +86-19930503282 , +86-19930503282
Website: https://www.chemicalbook.com/manufacturer/crovell/
Company Name: Xiamen AmoyChem Co., Ltd
Tel: +86-592-6051114 +8618959220845 , +8618959220845
Website: http://www.amoychem.com/
Company Name: Nanjing Baifuli Technology Co., Ltd.
Tel: +86-15335185688
Website: www.chemicalbook.com/ShowSupplierProductsList1787360/0.htm
Company Name: Xi'an Kono chem co., Ltd.,
Tel: 029-86107037 13289246953 , 13289246953
Website: www.konochem.com
Company Name: Hubei xin bonus chemical co. LTD
Tel: 86-13657291602
Website: www.chemicalbook.com/ShowSupplierProductsList1549548/0.htm
Company Name: BOC Sciences
Tel: +1-631-485-4226
Website: www.bocsci.com/
Tags:2595-05-3 Related Product Information
37091-65-9 2595-97-3 2595-05-3