Реакция #88967

Уравнение реакции

iodomethane

diacetone α-D-glucose

THF

NaH

THF

carbon disulfide

→

O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate

Условия реакции

Обработка

1. 1
   Другоеtemperature below 15° C
2. 2
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 1 hour
3. 3
   workup.STIRRINGstirred at room temperature for another 2 hours
4. 4
   Другоеquenched by saturated NH4Cl solution (70 mL)
5. 5
   Экстракцияextracted with EtOAc (100 mL) twice
6. 6
   СушкаThe combined organic layers were dried over Na2SO4
7. 7
   Концентрированиеconcentrated in vacuo
8. 8
   ДругоеThe residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether)

Методика

To a suspension of NaH (60% in mineral oil, 4 g, 100 mmol) in THF (80 mL) was added a solution of diacetone-α-D-glucose (10.5 g, 40 mmol) and imidazole (136 mg, 2 mmol) in THF (20 mL) dropwise while keeping inner temperature below 15° C. The formed mixture was stirred at 10° C. for 15 minutes. To the previous mixture was added carbon disulfide (14.8 g, 200 mmol) and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was added iodomethane (24.6 g, 200 mmol) and stirred at room temperature for another 2 hours, then quenched by saturated NH4Cl solution (70 mL) and extracted with EtOAc (100 mL) twice. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether) to afford 14.6 g of O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate (compound 1a) as a colorless oil.

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