Water → Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-((2,3,6-trideoxy-3-(dimethylamino)hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate

HRID 435457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 435457
[CH3:1][C@@H:2]1[O:7][C@@H:6]([O:8][C@@H:9]2[C:14]3[C:15]([OH:30])=[C:16]4[C:23](=[O:24])[C:22]5[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:21]=5[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[C@@H:12]([C:31]([O:33][CH3:34])=[O:32])[C@@:11]([OH:36])([CH3:35])[CH2:10]2)[CH2:5][C@H:4]([N:37]([CH3:39])[CH3:38])[C@@H:3]1[O:40][C@@H]1O[C@@H](C)[C@@H](O[C@@H]2O[C@@H](C)C(=O)CC2)[C@@H](O)C1.Cl.CO.[OH-].[Na+].O>CC(C)=O.CO>[CH3:1][CH:2]1[O:7][CH:6]([O:8][CH:9]2[C:14]3[C:15]([OH:30])=[C:16]4[C:23](=[O:24])[C:22]5[C:25]([OH:29])=[CH:26][CH:27]=[CH:28][C:21]=5[C:19](=[O:20])[C:17]4=[CH:18][C:13]=3[CH:12]([C:31]([O:33][CH3:34])=[O:32])[C:11]([OH:36])([CH3:35])[CH2:10]2)[CH2:5][CH:4]([N:37]([CH3:39])[CH3:38])[CH:3]1[OH:40]

Komponenten

7

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 155838Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-({2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-(6-methyl-5-oxooxan-2-yl)hexopyranosyl]-3-(dimethylamino)hexopyranosyl}oxy)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylateHCID 21893726Hydrochloride methanol

Produkt 1

HCID 174252Methyl 2,5,7-trihydroxy-2-methyl-6,11-dioxo-4-((2,3,6-trideoxy-3-(dimethylamino)hexopyranosyl)oxy)-1,2,3,4,6,11-hexahydrotetracene-1-carboxylateAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 100 mg of auramycin A in 20 ml of acetone and 1 ml of methanol was added 1 ml of 0.2 N hydrochloric acid-methanol with stirring and reacted at room temperature for 40 minutes. The reaction mixture was neutralised by dilute sodium hydroxide solution and 20 ml of water was added and extracted with 20 ml of chloroform twice. The extracts were combined and concentrated to a small volume in vacuo. The concentrate was chromatographed by a column packed with silica gel (chloroform:methanol, 95:5). The fractions containing auramycin D were concentrated in vacuo to give 43 mg of auramycin D.

Aufarbeitung

  1. customreacted at room temperature for 40 minutes
  2. additionwas added
  3. extractionextracted with 20 ml of chloroform twice
  4. concentrationconcentrated to a small volume in vacuo
  5. customThe concentrate was chromatographed by a column
  6. additionThe fractions containing auramycin D
  7. concentrationwere concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a87aa935df3d4311a30a6f0f46bb28a1
Quelldatensatz
uspto-grants-1983_08
Patentnummer
US04401812

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