Sulfuric Acid → (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
Reaction equation
[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]=1Participants
Procedure
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.
Sources & evidence
- ORD record
- ord-96992cd0460d4821a7e04f223c411f72
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05008381
Reaction notes
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