HCID 131716980, compound → HCID 11041589, compound

HRID 973527Notes

Reaction equation

HRID 973527 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

HCID 131716980HCID 131716980, compound

Product 1

HCID 11041589HCID 11041589, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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)

Workup

  1. temperatureThe solution is cooled to room temperature
  2. filtrationThe resin is filtered off
  3. temperaturethe filtrate is refluxed for 15 minutes with activated carbon (4.0 g)
  4. customCarbon is removed with a glass fiber
  5. filtrationfilter
  6. customthe filtrate is evaporated to dryness with ethanol
  7. temperatureThe white waxy residue is refluxed for 15 minutes with methanol (50ml)
  8. waitThe solution is stored overnight at 0° C
  9. filtrationThe product is filtered

Sources & evidence

ORD record
ord-82e7ec9054d04147a4e565086dfd15c1
Source dataset
uspto-grants-1991_11
Patent number
US05064672

Reaction notes

Loading…