Acetic Acid → (2R,3S,4S,5S)-5-(acetoxymethyl)tetrahydrofuran-2,3,4-triyl triacetate
Reaction equation
[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]Participants
8
Procedure
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.
Workup
- customBy recrystallizing from ethyl ether
Sources & evidence
- ORD record
- ord-77c4ed05c16c4c359fd204d04d4c9fac
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394935B2
Reaction notes
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