Chloroform → HCID 86745036, compound

HRID 728213Notes

Reaction equation

HRID 728213 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@@H:11](OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:28]=[N+:29]=[N-:30].[Na+].C(Cl)(Cl)Cl>CN(C)C=O>[N:28]([C@@H:11]1[CH2:10][C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:14]2[CH2:15][O:16][C@@H:12]1[O:13]2)=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 33557Sodium AzideHCID 86745035HCID 86745035, compound

Product 1

HCID 86745036HCID 86745036, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 1,6-anhydro-4-O-benzyl-3-deoxy-2-O-p-toluenesulphonyl-β-D-arabino-hexopyranose (See Preparative Example 3) (0.50 g) in N,N-dimethylformamide (10 ml) was added sodium azide (0.25 g) and the mixture was heated with stirring at 150° C. for 3 days. Chloroform was added and the mixture was washed with water (×4), dried (MgSO4) and concentrated to a syrup. Purification by flash chromatography gave the title compound (0.30 g), [α]D -14.8°; 13C-nmr data: 100.8 (C-1), 55.8 (C-2), 24.6 (C-3), 71.0 and 70.6 (C-4 and PhCH2O), 74.7 (C-5), 65.7 (C-6), 137.8, 128.4, and 127.7 (aromatic).

Workup

  1. temperaturethe mixture was heated
  2. washthe mixture was washed with water (×4)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a syrup
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-0748ad4633c54fb18bc1cb0733d6bce5
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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