HCID 10846754, compound → HCID 11041589, compound

HRID 1030035Notes

Reaction equation

HRID 1030035 reaction equation
O[CH2:2][C:3]1([CH2:14][OH:15])[O:10][C@@H:7]([O:8]C)[C@H:6]([OH:11])[C@@H:5]([OH:12])[C@H:4]1[OH:13]>S(=O)(=O)(O)O>[OH:15][CH2:14][C@@:3]12[CH2:2][O:8][C@@H:7]([O:10]1)[C@H:6]([OH:11])[C@@H:5]([OH:12])[C@H:4]2[OH:13]

Participants

3

Reactant 1

HCID 10846754HCID 10846754, 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-hexopyranoside (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-), 250 ml). The filtrate is removed from the resin, 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 (50 ml). The solution is stored overnight at 0° C. The product crystal are filtered to yield 20.0 g (39.6%) of 5-C-hydroxymethyl 1,6-anhydro-β-L-altropyranose (4). M.P.=166.5° C.-168.5° C. [α]D23 =+145.1 (7.2 c. in water)

Workup

  1. temperatureThe solution is cooled to room temperature
  2. customThe filtrate is removed from the resin
  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 (50 ml)
  8. waitThe solution is stored overnight at 0° C
  9. filtrationThe product crystal are filtered

Sources & evidence

ORD record
ord-654710d647f54d308ffe66b2672564c6
Source dataset
uspto-grants-1992_04
Patent number
US05104797

Reaction notes

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