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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1944790Erstellt: 26. Oktober 2026

Sulfuric Acid → (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate

https://huagongshe.com/reaction/1944790

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktSulfuric AcidHCID 1118—
EduktLithium CarbonateHCID 11125—
EduktL-RiboseHCID 90428—
Edukt1,2,3,5-tetra-O-acetyl-L-ribofuranoseHCID 11493434—
LösungsmittelAcetic AcidHCID 176—
LösungsmittelMethanolHCID 887—
LösungsmittelWaterHCID 962—
LösungsmittelIsopropanolHCID 3776—
LösungsmittelAcetic AnhydrideHCID 7918—
Produkt(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateHCID 90810060%

Reaktionsschritte

In Non-Patent Document 6, L-ribose is used as a starting material, the methylation of the hydroxyl group at 1-position is carried out in methanol in the presence of sulfuric acid, the resultant mixture is then treated with lithium carbonate, the acetylation is then carried out in acetic acid and acetic anhydride, and concentrated sulfuric acid and acetic anhydride are further added thereto to carry out the acetolysis. A crude product is a mixture of α/β-anomers of 1,2,3,5-tetra-O-acetyl-L-ribofuranose. The crude product is treated with water and isopropyl alcohol to obtain 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose at a total yield of 60%.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08394935B2
Quelldatensatzuspto-grants-2013_03
ORD IDord-9025124fd92c45129b3beb332837a7c3
Quellennotizuspto-grants-2013_03