Reacción #310524

ord-c70689879d0447d9868e14808acbb776

Ecuación de reacción

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
Rendimiento 99.0%

Reactantes

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

Reactivos

Ninguno

Disolventes

CO
methanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto yield a homogeneous solution which
  2. 2
    Temperaturawas refluxed for 11/2 h
  3. 3
    OtroReaction
  4. 4
    TemperaturaAfter cooling to 0°
  5. 5
    ConcentraciónThe resultant mixture (primarily rebaudioside C) was then concentrated to dryness
  6. 6
    Otrothe residue recrystallized from water

Procedimiento

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 11/2 h. Reaction was than judged complete by TLC analysis. After cooling to 0°; the reaction mixture was acidified to pH3 with 10% H2SO4. The resultant mixture (primarily rebaudioside C) was then concentrated to dryness and the residue recrystallized from water to give 150 mg (99%) of pure rebaudioside C.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04353889uspto-grants-1982_10