1,2,3,5-Tetraacetyl-β-D-ribofuranose
(2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate · TETRAACETYLRIBOFURANOSE · beta-D-Ribofuranose · 1,2,3,5-TETRA-O-ACETYL-BETA-D-RIBOFURANOSE · TETRA-O-ACETYL-BETA-D-RIBOFURANOSE · 1,2,3,5-Tetraacetate · 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose · 1,2,3,5-tera-O-acetyl-beta-D-ribofuranose
Identifikatoren & physikalische Daten
| CAS No. | 13035-61-5 |
|---|---|
| Summenformel | C13H18O9 |
| Durchschnittliche Molmasse | 318,28 g/mol |
| Monoisotopische Masse | 318,09508215 g/mol |
| SMILES | CC(=O)OC[C@H]1O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H]1OC(C)=O |
| InChIKey | IHNHAHWGVLXCCI-FDYHWXHSSA-N |
| PubChem CID | 83064 |
| ChEMBL | CHEMBL3183254 |
| EC No. | 235-898-5 |
| DTXSID | DTXSID9057632 |
| Lokaler Name | 1,2,3,5-Tetraacetyl-β-D-ribofuranose |
Chemische & physikalische Eigenschaften
| XLogP | 0,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 114 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 9 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 458 |
| Schmelzpunkt | 81-83 °C(lit.) |
| Siedepunkt | 417.45°C (rough estimate) |
| Dichte | 1.4171 (rough estimate) |
| Brechungsindex | -14.5 ° (C=5, MeOH) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Löslichkeit | Chloroform (Sparingly), Methanol (Slightly) |
| Aggregatzustand | Crystalline Powder |
| Farbe | White to almost white |
| 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 Datenbank | 13035-61-5(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 72.7% (8 of 11) of all reports.WarningH315 (27.3%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (27.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (27.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 11 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 8 of 11 reports by companies.There are 3 notifications provided by 3 of 11 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 18-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26235 |
| Hazard Classes and Categories | Skin Irrit. 2 (27.3%)Eye Irrit. 2 (27.3%)STOT SE 3 (27.3%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29400090 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 22-24/25-36-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
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.
Verwenden
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.