Acetic Anhydride → Saikosaponin B2

HRID 2073582

Reaktionsgleichung

Reaktionsgleichung von HRID 2073582
[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C@:14]([CH2:16][OH:17])([CH3:15])[C@@H:13]3[CH2:18][CH2:19][C@@:20]4([CH3:40])[C@:25]5([CH3:39])[CH2:26][C@@H:27]([OH:38])[C@:28]67[CH2:36][O:37][C@:24]5([C@@H:29]6[CH2:30][C:31]([CH3:35])([CH3:34])[CH2:32][CH2:33]7)[CH:23]=[CH:22][C@@H:21]4[C@@:12]3([CH3:41])[CH2:11][CH2:10]2)[C@H:5]([OH:42])[C@@H:4]([O:43][C@@H:44]2[O:49][C@H:48]([CH2:50][OH:51])[C@@H:47]([OH:52])[C@H:46]([OH:53])[C@H:45]2[OH:54])[C@H:3]1[OH:55].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C@:14]([CH2:16][OH:17])([CH3:15])[C@@H:13]3[CH2:18][CH2:19][C@@:20]4([CH3:40])[C@@:25]5([CH3:39])[C:24](=[C:29]6[C@@:28]([CH2:36][OH:37])([C@H:27]([OH:38])[CH2:26]5)[CH2:33][CH2:32][C:31]([CH3:35])([CH3:34])[CH2:30]6)[CH:23]=[CH:22][C@@H:21]4[C@@:12]3([CH3:41])[CH2:11][CH2:10]2)[C@H:5]([OH:42])[C@@H:4]([O:43][C@@H:44]2[O:49][C@H:48]([CH2:50][OH:51])[C@@H:47]([OH:52])[C@H:46]([OH:53])[C@H:45]2[OH:54])[C@H:3]1[OH:55]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 107793Saikosaponin D2×

Produkt 1

HCID 21637642Saikosaponin B2

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

By way of example, the fully acetylated saikosaponin d can be obtained by adding 10 to 20 ml of acetic anhydride to a solution of saikosaponin d in 10 to 20 ml/g of pyridine and allowing the mixture to stand at 10° C. to 50° C. for 3 to 16 hours. When this reaction mixture is stirred with a 1 to 40% (w/w) aqueous solution of ferric chloride at 10° C. to 40° C. for 1 to 10 hours for cleavage of the ether ring, there is obtained the acetylated saikosaponin b2 in which only the hydroxy group in the 28 position is free. This product is subjected to the above-described phosphorylation reaction with DPC and, then, to hydrolysis of the acetyl groups under alkaline conditions (pH 9-14, preferably pH 10-13), whereby the salt of saikosaponin b2 -28-(dihydrogen phosphate) is obtained. In the same manner as above, a salt of saikosaponin b1 -28-(dihydrogen phosphate) can be obtained from saikosaponin a, and a salt of saikosaponin h-28-(dihydrogen phosphate) from saikosaponin c.

Quellen und Nachweise

ORD-Eintrag
ord-49d87ccedee044a78c5181e703369bf4
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04918171

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