Reaktion #2082615

ord-f93ff7a2198244a08c787ce082cd4e12

Reaktionsgleichung

O=S(=O)(O)O
H2SO4
C=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2CC[C@]1(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O)C3
Rebaudioside A
[K+].[OH-]
KOH
→
C=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2CC[C@]1(O[C@@H]1O[C@H](C)[C@@H](O)[C@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O)C3
rebaudioside C
Ausbeute 99.0%

Edukte

O=S(=O)(O)O
H2SO4
C=C1C[C@@]23CC[C@H]4[C@@](C)(CCC[C@@]4(C)C(=O)O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H]2CC[C@]1(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O)C3
Rebaudioside A
[K+].[OH-]
KOH
—
resultant mixture

Reagenzien

Keine

Lösungsmittel

CO
methanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeto yield a homogeneous solution which
  2. 2
    Temperaturwas refluxed for 1.5 hours
  3. 3
    SonstigeReaction
  4. 4
    TemperaturAfter cooling to 0°
  5. 5
    EinengenThe resultant mixture was then concentrated to dryness
  6. 6
    Sonstigethe residue recrystallized from water

Vorschrift

Rebaudioside A (0.2 mmol, 183 mg) was transferred to a 15 ml flask. Four ml each of 10% KOH and methanol were added and the resultant mixture heated to yield a homogeneous solution which was refluxed for 1.5 hours. Reaction was then judged complete by TLC analysis. After cooling to 0°; the reaction mixture was acidified to pH 3 with 10% H2SO4. The resultant mixture was then concentrated to dryness and the residue recrystallized from water to give 150 mg (99%) of pure rebaudioside C.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04404367uspto-grants-1983_09