Sodium Acetate → L-Ribofuranoside, methyl

HRID 1944793Notes

Reaction equation

HRID 1944793 reaction equation
[OH:1][CH:2]1[O:8][C@@H:7]([CH2:9][OH:10])[C@H:5]([OH:6])[C@@H:3]1[OH:4].[C:11]([O-])(=O)C.[Na+]>CO.S(=O)(=O)(O)O>[CH3:11][O:1][CH:2]1[O:8][C@@H:7]([CH2:9][OH:10])[C@H:5]([OH:6])[C@@H:3]1[OH:4]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 11804933L-ribofuranose

Product 1

HCID 11008257L-Ribofuranoside, methylYield 649.2%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent2×

Procedure

L-ribofuranose (20.0 g; 132 mmol) and methanol (226 g) were added to a 1,000-mL flask. Thereafter, concentrated sulfuric acid (1.49 g; 0.11 equivalents) dissolved in methanol (21.2 g) was slowly added dropwise thereto. The obtained mixture was reacted at room temperature for 5 hours. Thereafter, sodium acetate (2.40 g) was added to the reaction product for neutralization, and it was then concentrated under reduced pressure, so as to obtain 31.18 g of crude 1-O-methyl-L-ribofuranose as a whitish oily substance.

Workup

  1. additionwas slowly added dropwise
  2. customThe obtained mixture was reacted at room temperature for 5 hours
  3. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e0b7650ccb0492697b353254c903a88
Source dataset
uspto-grants-2013_03
Patent number
US08394935B2

Reaction notes

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