反应 #74475

反应方程式

2-chloro-5-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-1,3,4-thiadiazole

2-Chloro-5-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-1,3,4-thiadiazole

sodium methanethiolate

→

title compound

收率 77.0%

2-(2-Chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-5-(methylthio)-1,3,4-thiadiazole

收率 77.0%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   温度After cooling to 0° C.
2. 2
   其他the reaction was quenched with hydrochloric acid (1.0 M)
3. 3
   workup.ADDITIONdiluted with ethyl acetate and water
4. 4
   其他The organic layer was separated
5. 5
   萃取the aqueous layer was extracted with ethyl acetate
6. 6
   洗涤The combined organic layers were washed with brine
7. 7
   干燥dried over magnesium sulfate
8. 8
   过滤filtered
9. 9
   浓缩concentrated in vacuo
10. 10
    其他The residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes)

实验过程

To a solution of 2-chloro-5-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyl)-1,3,4-thiadiazole (419 mg, 0.55 mmol) from Step 2 in tetrahydrofuran (10 mL) was added sodium methanethiolate (77 mg, 1.1 mmol). The resulting mixture was stirred at ambient temperature overnight. After cooling to 0° C., the reaction was quenched with hydrochloric acid (1.0 M) and diluted with ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes) to yield the title compound (331 mg, 0.42 mmol, 77%) as a yellow oil. MH+ 779.

来源