Acetone → 2,3-O-Isopropylidene-D-ribofuranose

HRID 512125Notes

Reaction equation

HRID 512125 reaction equation
S(=O)(=O)(O)O.[O:6]=[CH:7][C@@H:8]([C@@H:10]([C@@H:12]([CH2:14][OH:15])[OH:13])[OH:11])[OH:9].C(=O)([O-])[O-].[Na+].[Na+].[CH3:22][C:23]([CH3:25])=O>>[CH3:22][C:23]1([CH3:25])[O:9][C@@H:8]2[C@@H:10]([C@@H:12]([CH2:14][OH:15])[O:13][CH:7]2[OH:6])[O:11]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 5311110Aldehydo-D-ribose

Product 1

HCID 110087122,3-O-Isopropylidene-D-ribofuranose

Procedure

Concentrated sulfuric acid (0.3 mL) was added to a suspension of D-ribose (12.5 g, 83 mmol) in acetone (125 mL). The reaction mixture was stirred at room temperature for 90 min to obtain a clear solution which was then neutralized with saturated aqueous sodium carbonate. The mixture was filtered over Celite® and concentrated in vacuo.

Workup

  1. customto obtain a clear solution which
  2. filtrationThe mixture was filtered over Celite®
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f3c57d804c546198270d72a323ed064
Source dataset
uspto-grants-2015_08
Patent number
US09102634B2

Reaction notes

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