Réaction #6528

Équation de réaction

amine

Methyl 3,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulofuranoside

sodium bicarbonate

benzylchloroformate

→

Methyl N-benzyloxycarbonyl-3,5-di-O-benzyl-2,6-dideoxy-2,6-imino-L-gulofuranoside

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   AutreThe aqueous phase was then separated
2. 2
   Lavagewashed with diethyl ether (3×10 ml)
3. 3
   SéchageThe combined ethereal layers were then dried (sodium sulphate)
4. 4
   Autrethe solvent removed in vacuo
5. 5
   AutrePurification by flash chromatography (0-50%, diethyl ether/hexane)

Mode opératoire

To the crude amine (15), in a solution of diethyl ether:saturated sodium bicarbonate (3:2, 20 ml), was added benzylchloroformate (0.2 ml, 1.2 mmol). The reaction was then stirred, at such a rate as to make it one phase, for 2 hours. The aqueous phase was then separated and washed with diethyl ether (3×10 ml). The combined ethereal layers were then dried (sodium sulphate) and the solvent removed in vacuo. Purification by flash chromatography (0-50%, diethyl ether/hexane) then yielded methyl N-benzyloxycarbonyl-3,5-di-O-benzyl-2,6-deoxy-2,6-imino-L-gulofuranoside (16), as a colorless oil (200 mg, 67% from azidotriflate). νmax (CHCl3): 1685, 750, 700 cm-1.

Source