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

HRID 1944790

Reaction equation

HRID 1944790 reaction equation
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]

Participants

10

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 7918Acetic AnhydrideSolvent2×

Procedure

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%.

Sources & evidence

ORD record
ord-9025124fd92c45129b3beb332837a7c3
Source dataset
uspto-grants-2013_03
Patent number
US08394935B2

Linked notes

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