Hydrochloric Acid → Methyl 2-deoxy-α-D-erythro-pentofuranoside

HRID 1734118Notes

Reaction equation

HRID 1734118 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]1

Participants

5

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

  1. concentrationthe resultant was concentrated
  2. additionTo the residue, 100 ml of toluene and 100 ml of pyridine were added
  3. dissolutionto dissolve the residue
  4. 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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