The DOI matches its Crossref record; 5 of the 5 references it cites were found in a registry or an index.
1-Benzenesulfinyl Piperidine/Trifluoromethanesulfonic Anhydride: A Potent Combination of Shelf-Stable Reagents for the Low-Temperature Conversion of Thioglycosides to Glycosyl Triflates and for the Formation of Diverse Glycosidic Linkages
Abstract
The combination of 1-benzenesulfinyl piperidine (BSP) and trifluoromethanesulfonic anhydride (Tf(2)O) forms a new, powerful, metal-free thiophile that can readily activate both armed and disarmed thioglycosides, via glycosyl triflates, in a matter of minutes at -60 degrees C in dichloromethane, in the presence of 2,4,6-tri-tert-butylpyrimidine (TTBP). The glycosyl triflates are rapidly and cleanly converted to glycosides, upon treatment with alcohols, in good yield and selectivity.
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Cites
Automated Solid-Phase Synthesis of Oligosaccharides
Plante, O. J., Palmacci, E. R., & Seeberger, P. H. (2001) · Science · doi:10.1126/science.1057324 · Cited by 933
Carbohydrates in Chemistry and Biology
Ernst, B., Hart, G. W., & Sinaý, P. (2000) · Wiley eBooks · doi:10.1002/9783527618255 · Cited by 594
Structural Basis of Trimannoside Recognition by Concanavalin A
Naismith, J. H., & Field, R. A. (1996) · Journal of Biological Chemistry · doi:10.1074/jbc.271.2.972 · Cited by 292
Redox State of Mars' Upper Mantle and Crust from Eu Anomalies in Shergottite Pyroxenes
Wadhwa, M. (2001) · Science · doi:10.1126/science.1057594 · Cited by 284
Dasgupta, F., & Garegg, P. J. (1988) · Carbohydrate Research · doi:10.1016/0008-6215(88)85071-7 · Cited by 160
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
NK T cells provide lipid antigen-specific cognate help for B cells
Leadbetter, E. A., Brigl, M., Illarionov, P., Cohen, N., Luteran, M. C., Pillai, S., Besra, G. S., & Brenner, M. B. (2008) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.0801375105 · Cited by 254
Roy, R., Murphy, P., & Gabius, H.-J. (2016) · Molecules · doi:10.3390/molecules21050629 · Cited by 76
Metadata
- Authors
- Crich, D., & Smith, M.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-08-21
- Volume
- 123
- Issue
- 37
- Pages
- 9015-9020
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2033521813
- Cited by
- 398
- References
- 5
- FWCI
- 9.89
- Type
- journal article
- Language
- en
- Open access
- closed
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- CoChat. (2026). Citation check: 1-Benzenesulfinyl Piperidine/Trifluoromethanesulfonic Anhydride: A Potent Combination of Shelf-Stable Reagents for the Low-Temperature Conversion of Thioglycosides to Glycosyl Triflates and for the Formation of Diverse Glycosidic Linkages. https://app.cochat.ai/papers/10.1021/ja0111481
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- Crich, D., & Smith, M. (2001). 1-Benzenesulfinyl Piperidine/Trifluoromethanesulfonic Anhydride: A Potent Combination of Shelf-Stable Reagents for the Low-Temperature Conversion of Thioglycosides to Glycosyl Triflates and for the Formation of Diverse Glycosidic Linkages. Journal of the American Chemical Society. https://doi.org/10.1021/ja0111481
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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