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Published on: April 4, 2014
Autoxidation Products of Betulonaldehyde
Sloan Ayers1, Tamas Benkovics1, Jonathan Marshall1
1Bristol-Myers Squibb Co. , Chemical & Synthetic Development, 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
Abstract:
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.
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