HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Methyl 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-carboxylate | HCID 155838 | — |
| Reactant | Hydrochloride methanol | HCID 21893726 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 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 | HCID 174252 | 61.8% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04401812 |
| Source dataset | uspto-grants-1983_08 |
| ORD ID | ord-a87aa935df3d4311a30a6f0f46bb28a1 |
| Source note | uspto-grants-1983_08 |