Tributylstannane → HCID 14311457, compound

HRID 2395086Notes

Reaction equation

HRID 2395086 reaction equation
[C:1]([O:9][C@@H:10]1[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@:16](C(SC)=S)(O)[C@@H:15]([CH2:32][O:33][C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:14][C@@H:11]1[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:1]([O:9][C@@H:10]1[C@@H:17]([O:18][C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:16][C@@H:15]([CH2:32][O:33][C:34](=[O:41])[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[O:14][C@@H:11]1[O:12][CH3:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 53939166HCID 53939166, compound

Product 1

HCID 14311457HCID 14311457, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the crude methyl 2,3,6-tri-O-benzoyl-4-(methylthio)thiocarbonyl-α-D-glucopyranoside (5.70 g, 9.55 mmol) in 120 mL of dry toluene was added AIBN (50 mg). Tributyl tin hydride (6.68 mL, 24.8 mmol) was added and the reaction was heated to reflux for 4 hours. The toluene was removed under reduced pressure. Acetonitrile (200 mL) was added and the mixture extracted with petroleum ether (5×100 mL) to remove all tin salts. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure to yield a clear colorless oil which solidified on standing. Purification by flash column chromatography using 20% ethyl acetate in petroleum ether as the eluant gave the target compound as a white solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 hours
  3. customThe toluene was removed under reduced pressure
  4. additionAcetonitrile (200 mL) was added
  5. extractionthe mixture extracted with petroleum ether (5×100 mL)
  6. customto remove all tin salts
  7. dry with materialAfter drying over anhydrous sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto yield a clear colorless oil which
  10. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-c4d1f7da4ea249d1a3eee4e61b3912db
Source dataset
uspto-grants-1998_09
Patent number
US05811512

Reaction notes

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