Methyl iodide → HCID 12688239, compound

HRID 60689Notes

Reaction equation

HRID 60689 reaction equation
[H-].[Na+].CC(C[C:7](O)([CH3:9])[CH3:8])=O.[OH:11][C@H:12]1[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:15]([OH:16])[C@H:13]1[OH:14].[C:23](=[S:25])=[S:24].I[CH3:27].[CH2:28]1[CH2:32]OC[CH2:29]1>N1C=CN=C1>[CH3:27][S:24][C:23](=[S:25])[O:22][C@@H:21]1[C@@H:13]2[C@@H:12]([O:11][C:28]([CH3:32])([CH3:29])[O:14]2)[O:20][C@@H:19]1[CH:17]1[CH2:15][O:16][C:7]([CH3:8])([CH3:9])[O:18]1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 131731797diacetone alpha-D-glucose

Product 1

HCID 12688239HCID 12688239, compound

Reagents, catalysts & solvents 1

HCID 795ImidazoleCatalyst

Conditions

Temperature
10 °C

Procedure

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.

Workup

  1. customtemperature below 15° C
  2. stirringthe reaction mixture was stirred at room temperature for 1 hour
  3. stirringstirred at room temperature for another 2 hours
  4. customquenched by saturated NH4Cl solution (70 mL)
  5. extractionextracted with EtOAc (100 mL) twice
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography on silica gel (eluting with 1:10 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-abd573a110714695bb0a4e7ab0b58dfd
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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