1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

• Gefahrenhinweise

  H315：Verursacht Hautreizungen.

  H319：Verursacht schwere Augenreizung.

  H335：Kann die Atemwege reizen.

• Sicherheit

  P261：Einatmen von Staub vermeiden.

  P305+P351+P338：BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R36/38:Reizt die Augen und die Haut.

• S-Sätze Betriebsanweisung:

  S22:Staub nicht einatmen.
  S24/25:Berührung mit den Augen und der Haut vermeiden.
  S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.

• Beschreibung

  β-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.

• Chemische Eigenschaften

  white to light yellow crystal powde

• Verwenden

  An inhibitor of neutrophil-keyhole limpet hemocyanin adhesion

• Definition

  The 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.

• Application

  Beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate, also known as 1-O-Acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose, is a ribose-derived compound used in nucleoside synthesis.

• Synthese

  Rac-(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-hydroxytetrahydrofuran-3,4-diyl dibenzoate was dissolved in dry pyridine, and the solution was slowly added dropwise with acetic anhydride in an ice water bath, then stirred for 30 minutes. Then, the ice water bath was removed, and the solution was stirred at room temperature for 7 hours and then heated to 40°C. This temperature was kept for an hour. The solution was added with broken ice and then stirred until the broken ice melted. The reaction solution was poured into ice water and extracted with chloroform. The organic layer was washed sequentially with ice water, pre-cooled sulfuric acid, and saturated sodium bicarbonate until the water layer showed weak alkaline, then washed with ice water until the water layer showed neutral, dried over anhydrous sodium sulfate for more than 4 hours, and then drawn off under reduced pressure, to obtain the light yellow syrup-like beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate (92.1%).
  

• läuterung methode

  Recrystallise it from EtOH or isoPrOH. [Helv Chim Acta 42 1171 1959, NMR: J Org Chem 33 1799 1968, IR: Chem Pharm Bull Jpn 11 188 1963, Beilstein 17/6 V 213.]

beta-D-Ribofuranose 1-acetate 2,3,5-tribenzoate Upstream-Materialien And Downstream Produkte

1-O-Acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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