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

HRID 1085234

反応式

HRID 1085234 の反応式
[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

参加物

6

反応物 3

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

生成物 3

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

実験手順

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.

出典と根拠

ORDレコード
ord-96992cd0460d4821a7e04f223c411f72
出典データセット
uspto-grants-1991_04
特許番号
US05008381

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