反应 #1350596

反应方程式

neomycin sulfate

HBr

→

2-deoxystreptamine hydrobromide

收率 61.0%

2-Deoxystreptamine Hydrobromide

收率 61.0%

反应条件

后处理

1. 1
   浓缩The solution is concentrated to dryness at 60° C. under reduced pressure
2. 2
   workup.DISSOLUTIONThe residue is dissolved into water (H2O) (100 mL), and activated charcoal (10 g)
3. 3
   workup.ADDITIONis added
4. 4
   其他the charcoal is removed by filtration through Celite
5. 5
   浓缩the solution is concentrated to a syrup
6. 6
   workup.ADDITIONMethanol (100 mL) is added
7. 7
   workup.STIRRINGthe mixture is stirred for 2 hours t room temperature
8. 8
   过滤The solid product is filtered

实验过程

A solution of neomycin sulfate (20 g, 20.8 mmol) in HBr (150 mL, 48%) is stirred under reflux at 100° C. for 40 hours. The solution is concentrated to dryness at 60° C. under reduced pressure. The residue is dissolved into water (H2O) (100 mL), and activated charcoal (10 g) is added. After stirring at room temperature for 10 hours, the charcoal is removed by filtration through Celite, and the solution is concentrated to a syrup. Methanol (100 mL) is added and the mixture is stirred for 2 hours t room temperature. The solid product is filtered to give 2-deoxystreptamine hydrobromide 3 (4.1 g, 61%). Rf: 0.2 (CH3OH/NH4OH=4:1); 1H-NMR (D2O, 200 MHZ): d 1.95 (1H, ddd), 2.5 (1H, m), 3.2-3.6 (9H, m); 13C-NMR (D2O, 200 MHZ): d 40.0, 65.0, 87.2, 89.5. Ref. Georgiadas, M. P.; Constantinou-Kokotou, V. J. Carbohydr. Chem. 1991, 10, 739-746.

来源