1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate
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Grundinformationen
- CAS
6974-32-9- Standard-SMILES
CC(=O)O[C@@H]1O[C@H](COC(=O)c2ccccc2)[C@@H](OC(=O)c2ccccc2)[C@H]1OC(=O)c1ccccc1- InChIKey
GCZABPLTDYVJMP-CBUXHAPBSA-N- Summenformel
- C28H24O9
- Durchschnittliche Molmasse
- 504,5 g/mol
- Monoisotopische Masse
- 504,14203235
Namen und Bezeichner
- Bevorzugter Name
- beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate
- IUPAC
- [(2R,3R,4R,5S)-5-acetyloxy-3,4-dibenzoyloxyoxolan-2-yl]methyl benzoate
- Lokaler Name
- 1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
- Englischer Name
- beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate
- Summenformel
- C28H24O9
- Molmasse
- 504.48
Namen und Synonyme
6974-32-91-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose.beta.-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateEINECS 230-220-4NSC 23349beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoateDTXSID408843461-Acetyl-2,3,5-tribenzoyl-beta-D-ribofuranoseAcetyl-tribenzoyl-.beta.-d-ribofuranose1-Acetyl-2,3,5-tribenzoyl-.beta.-D-ribofuranose1-O-Acetyl-2,3,5-O-benzoyl-.beta.-d-ribofuranose1-O-Acetyl-2,3,5-tri-O-benzoyl-.beta.-D-ribofuranose
Weitere Namen anzeigen
1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranoseABR1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribose1-O-acetyl 2,3,5-tri-O-benzoyl-β-d-[UL-13C5]ribofuranoside1-Acetyl-21-O-AcetyLB-D-RIBOFURANOSE-β-D-ribofuranose
1-O-Acetyl-2,3,5-tri-O-benzyl-.beta.-D-ribofuranoseRefChem:119334DTXCID901023793Acetyl-tribenzoyl-beta-d-ribofuranose1-O-Acetyl-2,3,5-O-benzoyl-beta-d-ribofuranose1-O-Acetyl-2,3,5-tri-O-benzyl-beta-D-ribofuranose230-220-4GCZABPLTDYVJMP-CBUXHAPBSA-N
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 5,6
- Polarare Oberfläche (TPSA)
- 114 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 12
- Schwere Atome
- 37
- Formalladung
- 0
- Komplexität
- 793
Physikochemische Eigenschaften
- Schmelzpunkt
- 128 · 128-130 °C
- Siedepunkt
- 621 · 621.0±55.0 °C(Predicted)
- Dichte
- 1.35 · 1.35±0.1 g/cm3(Predicted)
- Brechungsindex
- 24 ° · 24 ° (C=1, Pyridine)
- storage temp.
- Sealed in dry,Room Temperature
- Löslichkeit
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated),
- Aggregatzustand
- Liquid
- Farbe
- Clear slightly yellow or greenish to brown
- BRN
- 100243 · 100243
- InChIKey
- GCZABPLTDYVJMP-CBUXHAPBSA-N
- SMILES
- C(OC)(=O)C1=CC=CC=C1[C@@H]1[C@@H](OC(=O)C2=CC=CC=C2)[C@@H](OC(=O)C2=CC=CC=C2)[C@H](OC(C)=O)O1 |&1:10,11,21,31,r|
- CAS Datenbank
- 6974 · 6974-32-9(CAS DataBase Reference)
- EPA chemische Informationen
- 1 · .beta.-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate (6974-32-9)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (4 of 4) of all reports.
Not Classified
Aggregated GHS information provided per 4 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information.beta.-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesNot Classified
Sicherheitsdaten
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29400090
- risk_code
- 36/38
- hazard_code
- Xi
- safety_code
- 22-24/25-37/39-26
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Verwendung und Herstellung
General Manufacturing Information.beta.-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate: ACTIVE
Anwendungen
Beschreibungβ-D-Ribofuranose 1-Acetate 2,3,5-Tribenzoate is an optically active ribose derivative. It is white to orange to green powder to crystals, slightly soluble in methanol, and can be used as a starting material for nucleoside synthesis. The substance is also used as an intermediate for Clofarabine, which belongs to a class of drugs called purine nucleoside antimetabolites and is used to treat acute lymphoblastic leukemia (ALL) in children and young adults aged 1 to 21 years.
VerwendenAn inhibitor of neutrophil-keyhole limpet hemocyanin adhesion
Vor- und nachgelagerte Produkte
Nachgelagerte Produkte
Ergänzende Hinweise
DefinitionThe commonly used 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate) can be employed in the glycosylation of 7-deazapurines when 7-halogenated nucleobases are used. Using common ribosugars such as 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose resulted in the formation of orthoamides when the pyrrole ring was not functionalized. The glycosylation yield and glycosylation position of 7-deazapurines with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose depends strongly on 7-substituents (H vs halogen) and amino protecting groups. It could be used to synthesize 5-Bromo-4-chloro-2-[(N2-isobutyryl){2,3,5-tri-O-benzoyl-β-Dribofuranosyl}]amino-7H-pyrrolo[2,3-d]pyrimidine.
Zugehörige Reaktionen
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