p-Toluenesulfonic acid → Anhydromaggiemycin

HRID 615849Notes

Reaction equation

HRID 615849 reaction equation
[CH3:1][CH2:2][C:3]1(O)[CH:26]([C:27]([O:29][CH3:30])=[O:28])[C:8]2[C:9]([OH:25])=[C:10]3[C:23](=[O:24])[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([OH:22])[C:16]=4[C:14](=[O:15])[C:11]3=[C:12]([OH:13])[C:7]=2[C:5](=[O:6])[CH2:4]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][CH2:2][C:3]1[CH:4]=[C:5]([OH:6])[C:7]2[C:12]([OH:13])=[C:11]3[C:14]([C:16]4[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:17]=4[C:23](=[O:24])[C:10]3=[C:9]([OH:25])[C:8]=2[C:26]=1[C:27]([O:29][CH3:30])=[O:28])=[O:15]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14524973HCID 14524973, compound

Product 1

HCID 124643AnhydromaggiemycinYield 84%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

When maggiemycin was refluxed with p-toluene sulfonic acid in benzene for 4 hours, anhydromaggiemycin, at a yield of 84%, was obtained that was identical to the natural product in all physicochemical properties. The preparation of these compounds is summarized in FIG. 10.

Sources & evidence

ORD record
ord-47c554bd1f2141cd99d6ce32616c9d95
Source dataset
uspto-grants-1985_02
Patent number
US04501699

Reaction notes

Loading…