Acetic Acid → 1,2,3,5-Tetraacetyl-beta-D-ribofuranose

HRID 1944788Notes

Reaction equation

HRID 1944788 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].S(=O)(=O)(O)O.C(O[C:20](=[O:22])[CH3:21])(=O)C.[C:23]([OH:26])(=O)[CH3:24]>CO.N1C=CC=CC=1>[C:2]([O:1][C@@H:2]1[O:8][C@H:7]([CH2:9][O:10][C:20](=[O:22])[CH3:21])[C@@H:5]([O:6][C:23](=[O:26])[CH3:24])[C@H:3]1[O:4][C:5](=[O:6])[CH3:7])(=[O:1])[CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric Acid2×HCID 7918Acetic Anhydride2×HCID 5311110Aldehydo-D-ribose

Product 1

HCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

In Non-Patent Document 5, D-ribose is used as a starting material, the alkylation of the hydroxyl group at 1-position is carried out in methanol in the presence of sulfuric 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 ethanol, 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose is obtained at a total yield of 55%. Moreover, the hydroxyl group at 1-position is methylated, and thereafter, acetylation and the subsequent acetolysis are carried out in acetic acid and acetic anhydride in the presence of concentrated sulfuric acid. Thereafter, by recrystallizing from ethanol, 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose is obtained at a total yield of 53%.

Workup

  1. customBy recrystallizing from ethanol

Sources & evidence

ORD record
ord-a39d3d6d05844f0abcc0b6f679b7c1c2
Source dataset
uspto-grants-2013_03
Patent number
US08394935B2

Reaction notes

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