Sodium Cyanide → HCID 178511094, compound

HRID 879934Notes

Reaction equation

HRID 879934 reaction equation
I[C:2]([C@@H:4]([C@H:6]([C@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5])=O.[C-:14]#[N:15].[Na+]>CN(C=O)C>[CH2-:2][C:4]([CH3:6])=[O:5].[CH2-:2][C:4]([CH3:6])=[O:5].[C:14]([CH2:2][C@H:4]([OH:5])[C@@H:6]([OH:7])[C@@H:8]([OH:9])[C@H:10]([OH:11])[CH:12]=[O:13])#[N:15]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 86637224HCID 86637224, compound

Product 1

HCID 178511094HCID 178511094, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 27 was prepared following a procedure by Streicher and Wunsch (Carbohydr. Res. 338(22): 2375-85 (2003)). Referring to Scheme 7, iodo-galactose (120 mg, 0.32 mmol) and NaCN (51 mg, 1 M) were heated to 110° C. in DMF for 12 h. The mixture was cooled, partitioned with CH2Cl2-water and the layers separated. The aqueous layer was further washed with CH2Cl2 (2×) and the combined organics washed with brine, dried (Na2SO4), filtered and concentrated to a brown oil. FCC purification (9:1 to 4:1 hexanes-EtOAc gradient) led to the pure product. Yield: 10 mg (12%). 1H-NMR (CDCl3) δ: 1.33 (s, 3H), 1.35 (s, 3H), 1.45 (s, 3H), 1.54 (s, 3H), 2.65 (dd, J =6.8 Hz, 16 Hz, 1H), 2.70 (dd, J=6.8 Hz, 16 Hz, 1H), 4.05 (dt, J=2.0 Hz, 7.2 Hz, 1H), 4.24 (dd, J=2.0 Hz, 8.0 Hz, 1H), 4.34 (dd, J=2.8 Hz, 4.8 Hz, 1H), 4.65 (dd, J=2.8 Hz, 8.0 Hz, 1H), 5.50 (d, J=5.2 Hz).

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned with CH2Cl2-water
  3. customthe layers separated
  4. washThe aqueous layer was further washed with CH2Cl2 (2×)
  5. washthe combined organics washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a brown oil
  9. customFCC purification (9:1 to 4:1 hexanes-EtOAc gradient)

Sources & evidence

ORD record
ord-feefa99cb94b478ea0ca4e7c1b64d0b8
Source dataset
uspto-grants-2015_03
Patent number
US08993326B2

Reaction notes

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