1,2,3,5-Tetraacetyl-beta-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
식별자 및 물리적 특성
| CAS No. | 13035-61-5 |
|---|---|
| 분자식 | C13H18O9 |
| 평균 분자량 | 318.28 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | 0.7 |
|---|---|
| 극성 표면적 | 114 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 9 |
| 회전 가능 결합 수 | 9 |
| 무거운 원자 수 | 22 |
| 형식 전하 | 0 |
| 복잡도 | 458 |
| 녹는점 | 81-83 °C(lit.) |
| 끓는 점 | 417.45°C (rough estimate) |
| 밀도 | 1.4171 (rough estimate) |
| 굴절률 | -14.5 ° (C=5, MeOH) |
| 저장 조건 | Inert atmosphere,Room Temperature |
| 용해도 | 클로로포름(소량으로 용해), 메탄올(약간 용해됨) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 흰색에서 거의 흰색 |
| 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| |
화학적 성질
beta-D-Ribofuranose 1,2,3,5-tetraacetate is white to almost white crystalline powder
안전 및 규제
| GHS 분류 | 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. |
|---|---|
| 규제 정보 | 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%) |
| 수질 위해 등급(WGK) | 3 |
| 관세 코드 | 29400090 |
| 위험 문구(R) | 36/37/38 |
| 위험 표시 | Xi |
| 안전 문구(S) | 22-24/25-36-26 |
| 저장 분류 | 11 - Combustible Solids |
용도
개요
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.
용도
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.