Chloroform → HCID 86745036, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence