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Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and 1H, 13C, and 19F NMR Spectroscopic Investigation
Abstract
The title question is addressed by low-temperature 1 H, 13 C, and 19 F NMR spectroscopies in CD 2 Cl 2 as well as by the preparation of authentic samples from glycopyranosyl bromides and AgOTf. At −78 °C glycosyl triflates are cleanly generated with either nonparticipating or particpating protecting groups at O-2. The glycosyl triflates identified in this manner were allowed to react with methanol, resulting in the formation of methyl glycosides. Glycosyl triflates were generated at −78 °C in CD 2 Cl 2 and allowed to warm gradually until decomposition was detected by 1 H and 19 F NMR spectroscopy. The decomposition temperature and products are functions of the protecting groups employed.
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Citations
Cited by
New Principles for Glycoside‐Bond Formation
Zhu, X., & Schmidt, R. R. (2009) · Angewandte Chemie International Edition · doi:10.1002/anie.200802036 · Cited by 957
Li, Y., & Yu, B. (2010) · Chemical Communications · doi:10.1039/c0cc00566e · Cited by 40
Metadata
- Authors
- Crich, D., & Sun, S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1997-11-01
- Volume
- 119
- Issue
- 46
- Pages
- 11217-11223
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2025708871
- Cited by
- 372
- References
- 0
- FWCI
- 8.04
- Type
- journal article
- Language
- en
- Open access
- closed
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- Crich, D., & Sun, S. (1997). Are Glycosyl Triflates Intermediates in the Sulfoxide Glycosylation Method? A Chemical and 1H, 13C, and 19F NMR Spectroscopic Investigation. Journal of the American Chemical Society. https://doi.org/10.1021/ja971239r
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