HCID 86588181, compound → (3R,4S,5R)-5-(5-Ethyl-3-isoxazolyl)tetrahydro-2,3,4-furantriol

HRID 1839258Notes

Reaction equation

HRID 1839258 reaction equation
C[O:2][C@H:3]1[C@@H:7]2[O:8]C(C)(C)[O:10][C@@H:6]2[C@@H:5]([C:13](=[N:19][OH:20])[CH2:14][C:15](=O)[CH2:16][CH3:17])[O:4]1>C(O)(=O)C>[CH2:16]([C:15]1[O:20][N:19]=[C:13]([C@H:5]2[O:4][CH:3]([OH:2])[C@H:7]([OH:8])[C@@H:6]2[OH:10])[CH:14]=1)[CH3:17]

Participants

3

Reactant 1

HCID 86588181HCID 86588181, compound

Product 1

HCID 45093395(3R,4S,5R)-5-(5-Ethyl-3-isoxazolyl)tetrahydro-2,3,4-furantriolYield 40.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

1-[(3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pentane-1,3-dione 1-oxime (0.5 g) was dissolved in aqueous acetic acid (18 mg) and the mixture heated at 100° C. for 2 h. The solution was cooled and concentrated in vacuo to afford a brown oil which was azeotroped with toluene. Purification by chromatography on silica gel (Varian Bondelut silica gel cartridge), eluting with (i) dichloromethane, (ii) ether, (iii) ethyl acetate, (iv) methanol, gave the title compound (150 mg).

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated in vacuo
  3. customto afford a brown oil which
  4. customwas azeotroped with toluene
  5. customPurification by chromatography on silica gel (Varian Bondelut silica gel cartridge)
  6. washeluting with (i) dichloromethane, (ii) ether, (iii) ethyl acetate, (iv) methanol

Sources & evidence

ORD record
ord-a9ee5453018a4e7684af6e88565d25e3
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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