Novel benzyl rearrangements in electrospray ionization multistage tandem mass spectra of benzyl 2′,3′- didehydro-2′,3′-dideoxythymidin-5′-yl H-phosphonate
✍ Scribed by Yi Chen; Xiaobin Sun; Hua Fu; Xiaohong Liu; Yufen Zhao
- Publisher
- John Wiley and Sons
- Year
- 2004
- Tongue
- English
- Weight
- 147 KB
- Volume
- 39
- Category
- Article
- ISSN
- 1076-5174
- DOI
- 10.1002/jms.643
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✦ Synopsis
Abstract
Several alkyl 2^′^,3^′^‐didehydro‐2^′^,3^′^‐dideoxythymidin‐5^′^‐yl H‐phosphonates were synthesized and analyzed by electrospray ionization multistage tandem mass spectrometry (ESI − MS^n^). Two kinds of novel benzyl rearrangement reactions were observed in ESI − MS^2^ of [M + H]^+^, [M + Na]^+^ and [M + K]^+^ of benzyl 2^′^,3^′^‐didehydro‐2^′^,3^′^‐dideoxythymidin‐5^′^‐yl H‐phosphonate. Results from tandem mass spectrometry, high‐resolution mass spectrometry and control experiments showed that the benzyl migration could undergo a four‐membered cyclic rearrangement reaction, and benzyl was essential in the process. Copyright © 2004 John Wiley & Sons, Ltd.