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

HRID 1944790

Reaktionsgleichung

Reaktionsgleichung von HRID 1944790
O=C[C@H]([C@H]([C@H](CO)O)O)O.S(=O)(=O)(O)O.C(=O)([O-])[O-].[Li+].[Li+].[C:22]([O:25][CH:26]1[O:38][C@@H:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:27]1[O:28][C:29](=[O:31])[CH3:30])(=[O:24])[CH3:23]>CO.C(O)(=O)C.C(OC(=O)C)(=O)C.C(O)(C)C.O>[C:22]([O:25][C@H:26]1[O:38][C@@H:37]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[C@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@@H:27]1[O:28][C:29](=[O:31])[CH3:30])(=[O:24])[CH3:23]

Komponenten

10

Edukt 4

HCID 1118Sulfuric Acid2×HCID 11125Lithium CarbonateHCID 90428L-RiboseHCID 114934341,2,3,5-tetra-O-acetyl-L-ribofuranose

Produkt 1

HCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 176Acetic AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel2×

Versuchsvorschrift

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%.

Quellen und Nachweise

ORD-Eintrag
ord-9025124fd92c45129b3beb332837a7c3
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394935B2

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