2595-05-3 Usage
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
Check Digit Verification of cas no
The CAS Registry Mumber 2595-05-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,5,9 and 5 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 2595-05:
(6*2)+(5*5)+(4*9)+(3*5)+(2*0)+(1*5)=93
93 % 10 = 3
So 2595-05-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6-,7-,8-,9-,10-/m1/s1
2595-05-3Relevant articles and documents
Microwave-assisted Synthesis of Hybrid Heterocyclics as Biological Potent Molecules
Srinivas,Sunitha,Vasumathi Reddy,Karthik,Rajesh Kumar
, p. 1564 - 1573 (2018)
A series of novel 5-((1H-benzo[d]imidazol-2-yl)methyl)-2-((3aR,5S,6S,6aR)-2,2-dimethyl-6-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-3-phenylthiazolidin-4-ones 9a–n has been synthesized from triazole-linked thiazolidinone derivatives 8a–g with o-phenylenediamine and characterized by IR, NMR, MS, and elemental analyses. Further, these compounds were screened for their antibacterial activity against Gram-positive bacteria, namely, Bacillus subtilis (ATCC 6633), Staphylococcus aureus (ATCC 6538p), and Micrococcus luteus (IFC 12708), and Gram-negative bacteria, namely, Proteus vulgaris (ATCC 3851), Salmonella typhimurium (ATCC 14028), and Escherichia coli (ATCC 25922). Among the screened compounds, compounds 9b, 9d, 9h, and 9i are highly active against almost all selected bacterial strains; the remaining compounds showed moderate to good activity and emerged as potential molecules for further development.
TLR7 AGONISTS
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Paragraph 0247; 0250; 0252, (2021/05/28)
The present invention relates to TLR7 agonists according to Formula I and their use in the treatment of diseases such as cancer and infectious disease.
Triethylamine-methanol mediated selective removal of oxophenylacetyl ester in saccharides
Rasool, Javeed Ur,Kumar, Atul,Ali, Asif,Ahmed, Qazi Naveed
, p. 338 - 347 (2021/01/29)
A highly selective, mild, and efficient method for the cleavage of oxophenylacetyl ester protected saccharides was developed using triethylamine in methanol at room temperature. The reagent proved successful against different labile groups like acetal, ketal, and PMB and also generated good yields of the desired saccharides bearing lipid esters. Further, we also observed DBU in methanol as an alternative reagent for the deprotection of acetyl, benzoyl, and oxophenylacetyl ester groups. This journal is
NOVEL PROCESS FOR MAKING ALLOFURANOSE FROM GLUCOFURANOSE
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Page/Page column 35-37; 46-48, (2019/12/15)
The present invention relates to the manufacture of allofuranose from glucofuranose as defined in the description and in the claim. Allofuranos is an intermediate in the manufacture of oligonucleotides which can be used as a medicament.