[N:1]([CH2:4][C@H:5]1[O:11][C:9]([OH:10])=[C:8]([OH:12])[C@@H:7]([OH:13])[CH2:6]1)=[N+:2]=[N-:3].CN(C)C=O.[H-].[Na+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CCOCC.CO>[N:1]([CH2:4][C@H:5]1[O:11][C:9]([OH:10])=[C:8]([OH:12])[C@@H:7]([O:13][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:6]1)=[N+:2]=[N-:3]Dissolve 7.5 gm. of the azide in 150 ml. of dry dimethylformamide and add 2.5 gm. of sodium hydride. Stir the mixture at 25°C. for 1 hour, then add 10 gm. of benzylbromide and stir the mixture at 25°C. for 6 hours. Add a 20% solution of methanol in ether and filter off the solids and wash with chloroform. Combine the filtrates and pour into water and extract with chloroform and dry over MgSO4. Evaporate the chloroform extract and chromatograph the resultant residue on a silica gel column (110 × 2.5 cm) using 5 % acetone in hexane as the eluant to obtain 6-azido-3-O-benzyl-4,6-dideoxy-D-threo-hex-1-enopyranose.
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