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

HRID 1944789

Reaktionsgleichung

Reaktionsgleichung von HRID 1944789
[O:1]=[CH:2][C@H:3]([C@H:5]([C@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].Cl.C(O[C:16](=[O:18])[CH3:17])(=O)C.S(=O)(=O)(O)O.[C:24]([OH:27])(=O)[CH3:25]>CO.N1C=CC=CC=1>[C:2]([O:1][C@H:2]1[O:8][C@@H:7]([CH2:9][O:10][C:16](=[O:18])[CH3:17])[C@H:5]([O:6][C:24](=[O:27])[CH3:25])[C@@H:3]1[O:4][C:5](=[O:6])[CH3:7])(=[O:1])[CH3:3]

Komponenten

8

Edukt 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 7918Acetic Anhydride2×HCID 90428L-Ribose

Produkt 1

HCID 908100(2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

In Non-Patent Document 2, L-ribose is used as a starting material, the alkylation of the hydroxyl group at 1-position is carried out in methanol that contains hydrochloric acid, the acetylation is carried out with acetic anhydride in pyridine, and the acetolysis is carried out in acetic acid and acetic anhydride in the presence of concentrated sulfuric acid. By recrystallizing from ethyl ether, 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose is obtained at a total yield of 57%. Hereinafter, in the present specification, 1,2,3,5-tetra-O-acetyl-β-L-ribofuranose may be referred to as β-L-TAR at times, and 1,2,3,5-tetra-O-acetyl-L-ribofuranose may be referred to as L-TAR at times.

Aufarbeitung

  1. customBy recrystallizing from ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-77c4ed05c16c4c359fd204d04d4c9fac
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394935B2

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