反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
A suspension of sodium hydride (71 mg, 1.8 mmol) in dry DMF (5 mL) was cooled to 0° C., and a solution of methyl 2-azido-4-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (33) (680 mg, 1.5 mmol) in dry DMF (5 mL) was added dropwise in 30 minutes. The resulting solution was stirred at room temperature for 30 minutes and 4-chlorobenzyl chloride (295 mg, 1.5 mmol) was added dropwise at 0° C. The reaction mixture was stirred at room temperature for 4.5 hours, cooled at 0° C. and dry methanol (1 mL) was added dropwise. The reaction mixture was concentrated under reduced pressure, then xylene (10 mL) was co-evaporated from the residue. The residue was treated with hexane (10 mL) and filtered to give methyl 2-azido-4-O-benzyl-6-O-(4-chlorobenzyl)-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (34) (620 mg, 71%).
WORKUP
后处理
- stirringThe reaction mixture was stirred at room temperature for 4.5 hours
- temperaturecooled at 0° C.
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionThe residue was treated with hexane (10 mL)
- filtrationfiltered