Hydrochloric Acid → Methyl 2-deoxy-α-D-erythro-pentofuranoside
Reaction equation
[O:1]=[CH:2][CH2:3][C@@H:4]([C@@H:6]([CH2:8][OH:9])[OH:7])[OH:5].Cl.[C:11](=O)([O-])O.[Na+]>CO>[O:1]([CH3:11])[C@H:2]1[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[CH2:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In 1.1 liters of methanol, 52 g of 2-deoxy-D-erythro-pentose was dissolved, and 3.8 ml of 1M hydrochloric acid solution in methanol was added at room temperature, followed by stirring the resulting solution at room temperature for 1 hour. To the reaction mixture, 1 g of sodium hydrogen carbonate was added and the resultant was concentrated after confirming that the solution was weakly basic. To the residue, 100 ml of toluene and 100 ml of pyridine were added to dissolve the residue and the resultant was concentrated. This operation was repeated totally twice to completely remove methanol. The thus obtained crude methyl 2-deoxy-α-D-erythro-pentofuranoside was used in the subsequent step without purification.
Workup
- concentrationthe resultant was concentrated
- additionTo the residue, 100 ml of toluene and 100 ml of pyridine were added
- dissolutionto dissolve the residue
- concentrationthe resultant was concentrated
Sources & evidence
- ORD record
- ord-1cff889ee47340589cf0eddccb76965b
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05532349
Reaction notes
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