반응 #88967

반응 방정식

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

반응 조건

후처리

1. 1
   기타temperature 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
   기타quenched by saturated NH4Cl solution (70 mL)
5. 5
   추출extracted with EtOAc (100 mL) twice
6. 6
   건조The combined organic layers were dried over Na2SO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether)

실험 절차

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.

출처