Boron trifluoride etherate → HCID 11481302, compound

HRID 1681124Notes

Reaction equation

HRID 1681124 reaction equation
C(O[C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][CH:7]=[CH:6]1)(=O)C.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>ClCCl>[C:12]([O:11][C@@H:10]1[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][CH2:7][CH:6]=[CH:5]1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 688303Tri-O-acetyl-D-glucal

Product 1

HCID 11481302HCID 11481302, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4,6-tri-O-acetyl-D-glucal (9.70 g; 35.6 mmol) was reacted at 0° C. with triethylsilane (4.96 g; 42.7 mmol) and borontrifluoride-etherate (3.04 g; 21.4 mmol) in dichloromethane (110 ml) under an atmosphere of argon for 5 minutes. The solution was poured into aqueous NaHCO3 solution and extracted several times with dichloromethane. The organic layer was dried (MgSO4), evaporated and the crude product purified by distillation.

Workup

  1. extractionextracted several times with dichloromethane
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated
  4. distillationthe crude product purified by distillation

Sources & evidence

ORD record
ord-e8a218f10adc486aa4dc6bb51488c28d
Source dataset
uspto-grants-1992_12
Patent number
US05169842

Reaction notes

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