Trifluoroacetic acid → An inositol

HRID 1251622Notes

Reaction equation

HRID 1251622 reaction equation
C[C@H]1O[C@H]([O:8][CH:9]2[C@@H:14]([OH:15])[C@@H:13]([OH:16])[CH:12]([OH:17])[C@H:11]([OH:18])[C@H:10]2[OH:19])[C@@H](N)C[C@@H]1N=C(N)C(O)=O.Cl.FC(F)(F)C(O)=O.[Mn]([O-])(=O)(=O)=O.[K+].C[C@H]1O[C@H](O[C@@H]2[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@H]2O)[C@@H](N)C[C@@H]1NC(C(O)=O)=N>O.C(O)(=O)C>[CH:9]1([OH:8])[CH:10]([OH:19])[CH:11]([OH:18])[CH:12]([OH:17])[CH:13]([OH:16])[CH:14]1[OH:15]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 88045Kasugamycin hydrochlorideHCID 516875Potassium PermanganateHCID 178461616HCID 178461616, compound

Product 1

HCID 892An inositolYield 20%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Kasugamycin hydrochloride (1 g) and 2N trifluoroacetic acid (5 mL) were combined and heated 4 h at 75° C., after which time silica gel TLC (solvent-butanol:acetic acid:water, 2:1:1; Visualization with potassium permanganate stain showed kasugamycin was still present. The solution was concentrated in vacuo. The hydrolysis product was purified in the usual manner using ion exchange resins and charcoal. D-chiro-inositol was obtained in 20% yield.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customThe hydrolysis product was purified in the usual manner

Sources & evidence

ORD record
ord-22c68d8a58114f49bdd71a6662b758c7
Source dataset
uspto-grants-2002_01
Patent number
US06342645B2

Reaction notes

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