54783-95-8 → 2-Amino-5-[glycyl(methyl)amino]-3,4,6-trihydroxycyclohexyl 2,6-diamino-2,3,4,6,7-pentadeoxyheptopyranoside
Reaction equation
[CH3:1][C@H:2]([NH2:28])[C@H:3]1[O:8][C@H:7]([O:9][C@H:10]2[C@H:15]([OH:16])[C@H:14]([N:17]([C:19]([CH2:21][NH2:22])=[O:20])[CH3:18])[C@@H:13]([O:23]C)[C@@H:12]([OH:25])[C@@H:11]2[NH2:26])[C@H:6]([NH2:27])[CH2:5][CH2:4]1.OS(O)(=O)=O.CC(N)C1OC(OC2C(O)C(NC)C(OC)C(O)C2N)C(N)CC1>>[CH3:1][CH:2]([NH2:28])[CH:3]1[O:8][CH:7]([O:9][CH:10]2[CH:15]([OH:16])[CH:14]([N:17]([C:19]([CH2:21][NH2:22])=[O:20])[CH3:18])[CH:13]([OH:23])[CH:12]([OH:25])[CH:11]2[NH2:26])[CH:6]([NH2:27])[CH2:5][CH2:4]1Participants
Procedure
For illustrative purposes, ths invention will be exemplified by the O-demethylation of fortimicin A and fortimicin B. Generally speaking, in the practice of the preferred embodiment of this invention, to obtain a 3-O-demethylfortimicin, for example 3-O-demethylfortimicin A, in approximately thirty percent yield, fortimicin A free base is dissolved in methylene chloride, preferably in an amount of from about 1.0 to about 100 mg (0.0025 to 0.25 mmole) of fortimicin A free base to each ml of an inert solvent such as methylene chloride, and the reaction mixture is cooled to a temperature of from about -72° to about 4° C., preferably about 0° C. and treated with from about 10 to about 100 equivalents of a boron trihalide selected from the group consisting of boron tribromide, boron trichloride and boron triiodide with stirring for about 10 to 60 minutes, preferably for about 30 minutes at a temperature of from about -72° to about 4° C., preferably at about 0° C.
Sources & evidence
- ORD record
- ord-f4c745343f5e4b06b3f5f515f0b33d9b
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04230848
Reaction notes
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