Boron trifluoride etherate → HCID 22856009, compound

HRID 863163Notes

Reaction equation

HRID 863163 reaction equation
C(O[CH:5]1[O:28][CH2:27][C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:15]([O:16][CH3:17])[C@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[Si]([C:33]#[N:34])(C)(C)C.B(F)(F)F.CCOCC>[N+](C)([O-])=O>[CH2:8]([O:7][C@@H:6]1[C@@H:15]([O:16][CH3:17])[C@H:18]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:27][O:28][CH:5]1[C:33]#[N:34])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 82115Trimethylsilyl cyanideHCID 54468030HCID 54468030, compound

Product 1

HCID 22856009HCID 22856009, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

To a stirred solution of 2,4-di-O-benzyl-3-O-methyl-a,b-D-xylopyranosyl acetate (20 g, 0.052 mole) and Me3SiCN (20 ml, 0.16 mole) in anhydrous nitromethane (300 ml) was added boron trifluoride etherate (1.0 g, 0.007 mole) at room temperature. After the mixture was stirred at room temperature for 30 min, the mixture was evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel using CH2C12 /AcOEt (99:1) as an eluent to give 2,4-di-O-benzyl-3-O-methyl-a,b-D-xylopyranosyl cyanide as colorless oil (13.0 g, 71% yield); EI-MS: m/z 353 (M+), 262 (M+ -Bn); 1 H-NMR of b-cyano-isomer (CDCl3)d; 3.15 (1H,dd,J=10, 11 Hz), 3.23 (1H,t,J=10 Hz), 3.49 (1H,m), 3.59 (1H,t,J=10 Hz), 3.66 (3H,s), 3.96 (1H,dd,J=5 & 11 Hz), 3.97 (1H,d,J=10 Hz), 4.61 (1H,d,J=12 Hz), 4.73 (1H,d,J=12 Hz), 4.84 (1H,d,J=11 Hz), 4.88 (1H,d,J=11 Hz), 7.29-7.42 (10H,m).

Workup

  1. customthe mixture was evaporated to dryness under reduced pressure
  2. customThe residue was chromatographed on silica gel using CH2C12 /AcOEt (99:1) as an eluent

Sources & evidence

ORD record
ord-a9809ea6061e4868b5819f07cfd46cb2
Source dataset
uspto-grants-1998_02
Patent number
US05719291

Reaction notes

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