Autoxidation Products of Betulonaldehyde.
Three major degradation products resulted from the exposure of betulonaldehyde (1) to air in solution at room temperature. From HRMS and NMR data, the products, which were isolated by preparative supercritical fluid chromatography (SFC), were identified as betulonic acid (2) and C-17 hydroperoxide epimers 3 (β-OOH) and 4 (α-OOH). For 3 and 4, the H-18 multiplet pattern of the isolated products established the configuration at C-17.
Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Sloan
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Ayers
Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Tamas
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Benkovics
Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Jonathan
J
Marshall
Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Yichen
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Tan
Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Neil A
NA
Strotman
Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Susanne
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Kiau
D000096:Acetone / Q000737:chemistry; D000388:Air; D002851:Chromatography, High Pressure Liquid; D025924:Chromatography, Supercritical Fluid; D006861:Hydrogen Peroxide / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry*; D000094062:Betulinic Acid
D000096:Acetone; D006861:Hydrogen Peroxide; D009828:Oleanolic Acid; D014315:Triterpenes; C000593278:betulonal; D000094062:Betulinic Acid; C118308:betulonic acid