تفاعل #74475

معادلة التفاعل

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

المردود 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

المردود 77.0%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooling to 0° C.
2. 2
   أخرىthe reaction was quenched with hydrochloric acid (1.0 M)
3. 3
   workup.ADDITIONdiluted with ethyl acetate and water
4. 4
   أخرىThe organic layer was separated
5. 5
   استخلاصthe aqueous layer was extracted with ethyl acetate
6. 6
   غسيلThe combined organic layers were washed with brine
7. 7
   تجفيفdried over magnesium sulfate
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated in vacuo
10. 10
    أخرىThe residue was purified on Biotage® purification apparatus (silica gel, 10 to 60% ethyl acetate in hexanes)

الإجراء التجريبي

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.

المصدر