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

HRID 1085234

반응식

HRID 1085234 반응식
[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

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 19233(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanalHCID 442428Naringin2회

생성물 3

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

실험 절차

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.

출처 및 근거

ORD 기록
ord-96992cd0460d4821a7e04f223c411f72
출처 데이터셋
uspto-grants-1991_04
특허 번호
US05008381

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