Tributylstannane → HCID 67930856, compound

HRID 728212Notes

Reaction equation

HRID 728212 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@H:11]([CH3:17])[C@H:10]1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].C(=S)=S.CI.C([SnH](CCCC)CCCC)CCC>C1COCC1.C1(C)C=CC=CC=1.CCOCC>[CH2:1]([O:8][C@@H:9]1[C@H:14]2[CH2:15][O:16][C@H:12]([O:13]2)[C@H:11]([CH3:17])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 5948TributylstannaneHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 11172736HCID 11172736, compound

Product 1

HCID 67930856HCID 67930856, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-methyl-β-D-glucopyranose (Tetrahedron Lett. 22 (1981) 4315-4318) (0.280 g) in dry THF (10 ml) was stirred while sodium hydride (1.2 eq) was added slowly. When effervescence had ceased, a large excess (>10 eq) of carbon disulphide was added and the solution was stirred at room temperature for 0.5 h. Methyl iodide (5 eq) was then added and the solution was stirred a further 0.5 h at room temperature. Ether (50 ml) was added and the mixture was washed with water. The aqueous washings were back extracted with ether and the combined ether extracts were washed with saturated aqueous sodium chloride and then dried (MgSO4) and concentrated to a light yellow syrup. This was dissolved in toluene (25 ml) and heated under reflux in a nitrogen atmosphere while tributyltin hydride (1.05 eq) in toluene (2 ml) was added slowly over 3 h. The solution was then heated under reflux for a further 16 h before being concentrated again to dryness.

Workup

  1. additionwas added slowly
  2. stirringthe solution was stirred a further 0.5 h at room temperature
  3. washthe mixture was washed with water
  4. extractionThe aqueous washings were back extracted with ether
  5. washthe combined ether extracts were washed with saturated aqueous sodium chloride
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a light yellow syrup
  8. dissolutionThis was dissolved in toluene (25 ml)
  9. temperatureheated
  10. additionwas added slowly over 3 h
  11. temperatureThe solution was then heated
  12. temperatureunder reflux for a further 16 h
  13. concentrationbefore being concentrated again to dryness

Sources & evidence

ORD record
ord-737c7ca823c84f4586549696e27fa731
Source dataset
uspto-grants-1991_09
Patent number
US05047518

Reaction notes

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