Tributylstannane → HCID 54240069, compound

HRID 1781261Notes

Reaction equation

HRID 1781261 reaction equation
C([O:4][CH:5]1[O:25][C@H:24]([C:26](=S)[O:27][C:28](=[O:30])[CH3:29])[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:11](OC2C=CC=CC=2)[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:8]([O:7][C@@H:6]1[CH2:11][C@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:24]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:25][CH:5]1[OH:4])(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 5948TributylstannaneHCID 22872936HCID 22872936, compound

Product 1

HCID 54240069HCID 54240069, compoundYield 135.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

1,2,4,6-tetra-O-acetyl-3-O-phenylthiono-glucopyranose (5.2 g) was dissolved in toluene (50 mL) and added to tributyl tin hydride (6.7 mL) and azobisisobutryonitrile (2.8 g). The reaction mixture was heated for 1 to 3 hours at 80° C. to provide for 3-deoxy-2,4,6-tri-O-acetyl-glucopyranose (4.5 g).

Sources & evidence

ORD record
ord-32ce6edd6bef4c65ac649d1e55c8191a
Source dataset
uspto-grants-1997_05
Patent number
US05633233

Reaction notes

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