Sulfuric Acid → (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal

HRID 1085234

Reaktionsgleichung

Reaktionsgleichung von HRID 1085234
[O:1]=[CH:2][C@@H:3]([C@@H:5]([C@H:7]([C@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4].C[C@@H]1O[C@@H]([O:19][C@H:20]2[C@H:25]([O:26][C:27]3[CH:28]=[C:29]([OH:45])[C:30]4[C:36](=[O:37])[CH2:35][C@@H:34]([C:38]5[CH:39]=[CH:40][C:41]([OH:44])=[CH:42][CH:43]=5)[O:33][C:31]=4[CH:32]=3)[O:24][C@H:23]([CH2:46][OH:47])[C@@H:22]([OH:48])[C@@H:21]2[OH:49])[C@H](O)[C@H](O)[C@H]1O.S(=O)(=O)(O)O>>[O:26]=[CH:25][C@@H:20]([C@H:21]([C@@H:22]([C@@H:23]([CH2:46][OH:47])[OH:24])[OH:48])[OH:49])[OH:19].[O:1]=[CH:2][C@@H:3]([C@@H:5]([C@H:7]([C@H:9]([CH3:11])[OH:10])[OH:8])[OH:6])[OH:4].[CH:43]1[C:38]([C@H:34]2[O:33][C:31]3[CH:32]=[C:27]([OH:26])[CH:28]=[C:29]([OH:45])[C:30]=3[C:36](=[O:37])[CH2:35]2)=[CH:39][CH:40]=[C:41]([OH:44])[CH:42]=1

Komponenten

6

Edukt 3

HCID 1118Sulfuric AcidHCID 19233(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanalHCID 442428Naringin2×

Produkt 3

HCID 19233(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanalHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 439246Naringenin

Versuchsvorschrift

Illustrative of a process for obtaining L-rhamnose from naringin is described by G. N. Pulley, et al., "Preparation of Rhamnose from Naringin", J. Amer. Chem. Soc., 61, p. 175 (1939), in which naringin is hydrolyzed by refluxing it with sulphuric acid (~3.7%). Glucose, L-rhamnose, naringenin and other reaction products are formed by the reaction. The reaction medium is cooled and naringenin, which is semi-solid, is separated from the cooled reaction medium. The remaining filtrate then is neutralized and heated to boiling in the presence of charcoal. The charcoal treated product is concentrated in vacuo and then is inoculated with yeast to ferment glucose. L-rhamnose is isolated from the fermented liquor by several steps of concentration in vacuo and washing.

Quellen und Nachweise

ORD-Eintrag
ord-96992cd0460d4821a7e04f223c411f72
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05008381

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