Sodium Cyanide → gamma-Mangostin

HRID 1257133Notes

Reaction equation

HRID 1257133 reaction equation
[CH3:1][C:2]([CH3:31])=[CH:3][CH2:4][C:5]1[C:10]([OH:11])=[C:9]2[C:12]([C:14]3[C:19]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])=[C:18]([O:25]C)[C:17]([OH:27])=[CH:16][C:15]=3[O:28][C:8]2=[CH:7][C:6]=1[O:29]C)=[O:13].CC(C)=CCC1C(O)=C2C(C3C(OC2=CC=1O)=CC(O)=C(OC)C=3CC=C(C)C)=O.[C-]#N.[Na+]>CS(C)=O>[CH3:1][C:2]([CH3:31])=[CH:3][CH2:4][C:5]1[C:6]([OH:29])=[CH:7][C:8]2[O:28][C:15]3[CH:16]=[C:17]([OH:27])[C:18]([OH:25])=[C:19]([CH2:20][CH:21]=[C:22]([CH3:23])[CH3:24])[C:14]=3[C:12](=[O:13])[C:9]=2[C:10]=1[OH:11]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 5281650MangostinHCID 5495925beta-Mangostin

Product 1

HCID 5464078gamma-Mangostin

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

O-Methyl γ-mangostins such as β-mangostin, 3-O-methyl-γ-mangostin, 6,7-dimethyl-γ-mangostin and 3,6,7-trimethyl-γ-mangostin are conveniently converted to α-mangostin first by demethylation using sodium cyanide (NaCN) in dimethyl sulfoxide (DMSO) and then subjected to inventive O-demethylation process to obtain γ-mangostin in good yield and high purity.

Sources & evidence

ORD record
ord-9325fcc757fb4aa9b585513b335079f4
Source dataset
uspto-grants-2013_06
Patent number
US08461360B2

Reaction notes

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