HCID 131716980, compound → HCID 11041589, compound
Reaction equation
C[C@:2]1([O:11][C:10]([CH2:14][OH:15])([CH2:12][OH:13])[C@H:8]([OH:9])[C@H:6]([OH:7])[C@H:4]1[OH:5])O>S(=O)(=O)(O)O>[OH:13][CH2:12][C@@:10]12[CH2:14][O:15][C@@H:2]([O:11]1)[C@H:4]([OH:5])[C@@H:6]([OH:7])[C@H:8]2[OH:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Methyl 5-C-hydroxymethyl-α-L-arabino-hexopyranose (3) (59.0 g 0.263 moles) is dissolved in 0.70M sulfuric acid (260 ml), and stirred at 100° C. for 90 minutes. The solution is cooled to room temperature and neutralized using an ion exchange resin (Amberlite IRA-400 (OH-). The resin is filtered off, and the filtrate is refluxed for 15 minutes with activated carbon (4.0 g). Carbon is removed with a glass fiber filter, and the filtrate is evaporated to dryness with ethanol. The white waxy residue is refluxed for 15 minutes with methanol (50ml). The solution is stored overnight at 0° C. The product is filtered to yield 20.0 g (39.6%) of 1,6-anhydro-5-C-hydroxymethyl-β-L-altropyranose (4)