反応 #6528

反応方程式

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

溶媒

diethyl ether

反応条件

後処理

1. 1
   その他The aqueous phase was then separated
2. 2
   洗浄washed with diethyl ether (3×10 ml)
3. 3
   乾燥The combined ethereal layers were then dried (sodium sulphate)
4. 4
   その他the solvent removed in vacuo
5. 5
   その他Purification by flash chromatography (0-50%, diethyl ether/hexane)

実験手順

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.

出典