1,2,3,5-Tetraacetyl-β-D-ribofuranose

1,2,3,5-Tetraacetyl-beta-D-ribofuranose

HCID 83064CAS 13035-61-5

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Grundinformationen

Standard-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
Summenformel: C13H18O9
Durchschnittliche Molmasse: 318,28 g/mol
Monoisotopische Masse: 318,09508215

Namen und Bezeichner

Bevorzugter Name: 1,2,3,5-Tetraacetyl-beta-D-ribofuranose
IUPAC: [(2R,3R,4R,5S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate
Lokaler Name: 1,2,3,5-Tetraacetyl-β-D-ribofuranose
Englischer Name: beta-D-Ribofuranose 1,2,3,5-tetraacetate
Summenformel: C13H18O9
Molmasse: 318.28

Namen und Synonyme

1,2,3,5-Tetraacetyl-beta-D-ribofuranoseEINECS 235-898-5beta-D-Ribofuranose, tetraacetateNSC 18738beta-D-Ribofuranose, 1,2,3,5-tetraacetateRefChem:410632235-898-513035-61-5beta-D-Ribofuranose 1,2,3,5-tetraacetate1,2,3,5-tetra-O-Acetyl-beta-D-ribofuranoseTetra-O-acetyl-beta-D-ribofuranoseMFCD00005358

Weitere Namen anzeigen

TETRAACETYLRIBOFURANOSEbeta-D-Ribofuranose1,2,3,5-Tetraacetate1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose1,2,3,5-tera-O-acetyl-beta-D-ribofuranoseBETA-D-RIBOFURANOSE 1,2,3,5-TETRA-O-ACETATE

(2S,3R,4R,5R)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate1,2,3,5-Tetraacetyl-.-d-ribofuranoseDTXSID9057632[(2R,3R,4R,5S)-3,4,5-triacetyloxyoxolan-2-yl]methyl acetate[(2R,3R,4R,5S)-3,4,5-triacetoxytetrahydrofuran-2-yl]methyl acetate1,2,3,5-Tetraacetyl-ss-D-ribofuranosebeta-d-ribofuranose-1,2,3,5-tetraacetate.beta.-D-Ribofuranose, tetraacetate

Datenbank-Bezeichner

CAS: 13035-61-5
PubChem CID: 83064
DTXSID: DTXSID9057632
ChEMBL: CHEMBL3183254
UNII: LVQ7CQ9SBR
EC Number: 235-898-5
Nikkaji: J259C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 0,7
Polarare Oberfläche (TPSA): 114 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 9
Frei drehbare Bindungen: 9
Schwere Atome: 22
Formalladung: 0
Komplexität: 458

Physikochemische Eigenschaften

Schmelzpunkt: 81 · 81-83 °C(lit.)
Siedepunkt: 417.45 °C · 417.45°C (rough estimate)
Dichte: 1.4171 · 1.4171 (rough estimate)
Brechungsindex: -14.5 ° · -14.5 ° (C=5, MeOH)
storage temp.: Inert atmosphere,Room Temperature
Löslichkeit: Chloroform (Sparingly), Methanol (Slightly)
Aggregatzustand: Crystalline Powder
Farbe: White to almost white
BRN: 94078 · 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 · 13035-61-5(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 72.7% (8 of 11) of all reports.

Warning

H315 (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 exposure; Respiratory 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.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 18-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26235

Hazard Classes and CategoriesSkin Irrit. 2 (27.3%)；Eye Irrit. 2 (27.3%)；STOT SE 3 (27.3%)

Regulatorische Informationen

Regulatory InformationStatus: Active Update: 18-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/26235

Sicherheitsdaten

wgk: 3
hs_code: 29400090
risk_code: 36/37/38
hazard_code: Xi
safety_code: 22-24/25-36-26
Speicherklasse: 11 - Combustible Solids

Chemie und Industrie

Anwendungen · 2 Einträge

Beschreibungbeta-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.

Verwendenbeta-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.