Sulfuric Acid → [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

HRID 1995433

Reaktionsgleichung

Reaktionsgleichung von HRID 1995433
[CH3:1][C@:2]12[C@@H:11]3[CH2:12][CH2:13][C@@:14]4([O:19][C@@H:20]5[O:25][C@H:24]([CH2:26]O)[C@@H:23]([OH:28])[C@H:22]([OH:29])[C@H:21]5[O:30][C@@H:31]5[O:36][C@H:35]([CH2:37][OH:38])[C@@H:34]([OH:39])[C@H:33]([O:40][C@@H:41]6[O:46][C@H:45]([CH2:47][OH:48])[C@@H:44]([OH:49])[C@H:43]([OH:50])[C@H:42]6[OH:51])[C@H:32]5[OH:52])[C:16]([CH2:18][C@@:10]3([CH2:15]4)[CH2:9][CH2:8][C@@H:7]1[C@@:6]([C:54]([O:56][C@@H:57]1[O:62][C@H:61]([CH2:63][OH:64])[C@@H:60]([OH:65])[C@H:59]([OH:66])[C@H:58]1[OH:67])=[O:55])([CH3:53])[CH2:5][CH2:4][CH2:3]2)=[CH2:17].[OH-].[K+].OS(O)(=O)=O>CO>[CH3:26][C@H:24]1[O:25][C@@H:20]([O:19][C@:14]23[C:16](=[CH2:17])[CH2:18][C@:10]4([CH2:15]2)[C@H:11]([C@@:2]2([CH3:1])[C@H:7]([CH2:8][CH2:9]4)[C@@:6]([C:54]([O:56][C@@H:57]4[O:62][C@H:61]([CH2:63][OH:64])[C@@H:60]([OH:65])[C@H:59]([OH:66])[C@H:58]4[OH:67])=[O:55])([CH3:53])[CH2:5][CH2:4][CH2:3]2)[CH2:12][CH2:13]3)[C@@H:21]([O:30][C@@H:31]2[O:36][C@H:35]([CH2:37][OH:38])[C@@H:34]([OH:39])[C@H:33]([O:40][C@@H:41]3[O:46][C@H:45]([CH2:47][OH:48])[C@@H:44]([OH:49])[C@H:43]([OH:50])[C@H:42]3[OH:51])[C@H:32]2[OH:52])[C@@H:22]([OH:29])[C@@H:23]1[OH:28]

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 44564215[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate

Produkt 1

HCID 44564216[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-13-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customto yield a homogeneous solution which
  2. temperaturewas refluxed for 1.5 hours
  3. customReaction
  4. temperatureAfter cooling to 0°
  5. concentrationThe resultant mixture was then concentrated to dryness
  6. customthe residue recrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-f93ff7a2198244a08c787ce082cd4e12
Quelldatensatz
uspto-grants-1983_09
Patentnummer
US04404367

Verknüpfte Notizen

Wird geladen…