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| beta-D-Ribofuranose 1,2,3,5-tetraacetate Basic information |
Product Name: | beta-D-Ribofuranose 1,2,3,5-tetraacetate | Synonyms: | -D-RIBOFURANOSE 1,2,3,5-TETRAACETATE;β-D-Ribo;1,2,3,5-Tetraacetylribofuranose;D-Ribose tetraacetate;Tetraacetyl-β-D-ribofuranose;beta-D-Ribofuranose 1,2,3,5-tetraacetate, 98+%;á-d-ribofuranose 1,2,3,5-tetraacetate;β-d-ribofuranose 1,2,3,5-tetra-o-acetate | CAS: | 13035-61-5 | MF: | C13H18O9 | MW: | 318.28 | EINECS: | 235-898-5 | Product Categories: | Nucleic acids;Pharmaceutical Intermediates;Sugars, Carbohydrates & Glucosides;Biochemistry;Nucleosides, Nucleotides & Related Reagents;O-Substituted Sugars;Ribose;Riboses and 2'-Deoxyriboses;Sugars;Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;13035-61-5;Glycon Biochem | Mol File: | 13035-61-5.mol |  |
| beta-D-Ribofuranose 1,2,3,5-tetraacetate Chemical Properties |
Melting point | 81-83 °C(lit.) | alpha | -15.4 º (c=7, MeOH) | Boiling point | 417.45°C (rough estimate) | density | 1.4171 (rough estimate) | refractive index | -14.5 ° (C=5, MeOH) | storage temp. | Inert atmosphere,Room Temperature | solubility | Chloroform (Sparingly), Methanol (Slightly) | form | Crystalline Powder | color | White to almost white | optical activity | [α]26/D 11.4°, c = 10 in chloroform | BRN | 94078 | InChI | InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11-,12-,13-/s3 | InChIKey | TTXVPMATRDJQIA-BKUVIOGVSA-N | SMILES | [C@@H]1(OC(=O)C)[C@@H](COC(=O)C)O[C@@H](OC(=O)C)[C@@H]1OC(=O)C |&1:0,5,12,17,r| | CAS DataBase Reference | 13035-61-5(CAS DataBase Reference) |
| beta-D-Ribofuranose 1,2,3,5-tetraacetate Usage And Synthesis |
Description | beta-D-Ribofuranose 1,2,3,5-tetraacetate is an acetylated derivative of ribose extensively used in carbohydrate research and synthetic chemistry. This compound features acetyl groups protecting the hydroxyl functionalities at positions 1, 2, 3, and 5 of the ribofuranose ring, which enhances its stability and solubility in organic solvents. β-D-Ribofuranose 1,2,3,5-tetraacetate is a crucial intermediate in synthesising nucleosides, nucleotides, and other complex carbohydrates. In research, it is utilized to study glycosylation mechanisms, focusing on the formation and stereochemistry of glycosidic bonds.
| Chemical Properties | beta-D-Ribofuranose 1,2,3,5-tetraacetate is white to almost white crystalline powder | Uses | beta-D-Ribofuranose 1,2,3,5-tetraacetate is used in the synthesis of 3-(β-D-ribofuranosyl)-2,3-dihydro-6H-1,3-oxazine-2,6-dione, a new pyrimidine nucleoside analog related to uridine. | Application | beta-D-Ribofuranose 1,2,3,5-tetraacetate, also known as 1,2,3,5-tetra-O-Acetyl-beta-D-ribofuranose (TAR), is an important organic reagent that can be used in the following pathways: (1) Used in low-energy electron-induced reactions in gas-phase TAR. Since the acetyl group in TAR is coupled to the five-membered ribose ring at relevant positions, it can serve as a suitable model compound for studying the reaction of sugar units in DNA to low-energy electrons[1]. (2) Used to prepare 1,2,3-tri-O-acetyl-β-d-ribofuranose by enzymatic deacetylation[2]. (3) Used in condensation reactions. In the presence of tin chloride, 1-hexene reacts with 1- O -acetyl-2,3,5-tri- O -benzoyl-β- d -ribofuranose ( 5b ) or 1,2,3,5-tetra- O -acetyl-β- d -ribofuranose ( 5a ) to form a complex mixture[3]. | References | [1] ILKO BALD. Low energy electron-induced reactions in gas phase 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose: a model system for the behavior of sugar in DNA.[J]. Journal of Chemical Physics, 2007. DOI:10.1063/1.2436873. [2] TUN-CHENG CHIEN; Ji W C. A convenient preparation of 1,2,3-tri-O-acetyl-β-d-ribofuranose by enzymatic regioselective 5-O-deacetylation of the peracetylated ribofuranose[J]. Carbohydrate Research, 2004. DOI:10.1016/j.carres.2004.01.010. [3] THOMAS L. CUPPS; Leroy B T; Dean S Wise. A further investigation of the stannic chloride-catalyzed condensation reaction of 1-hexene and 1,2,3,5-tetra-O-acyl-β-d-ribofuranoses[J]. Carbohydrate Research, 1983. DOI:10.1016/0008-6215(83)88135-X.
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| beta-D-Ribofuranose 1,2,3,5-tetraacetate Preparation Products And Raw materials |
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