β-Selective 2-Deoxy- and 2,6-Dideoxyglucosylations Catalyzed by Bis-Thioureas
We present methods for β-selective 2-deoxy- and 2,6-dideoxyglucosylations of natural products, carbohydrates, and amino acids using bis-thiourea hydrogen-bond-donor catalysts. Disarming ester protecting groups were necessary to counter the high reactivity of 2-deoxyglycosyl electrophiles toward non-stereospecific S<sub>N</sub>1 pathways. Alcohol and phenol nucleophiles with both base- and acid-sensitive functionalities were compatible with the catalytic protocol, enabling access to a wide array of 2-deoxy-β-<i>O</i>-glucosides.
Authors
- Peyton D. Beyer (ORCID: https://orcid.org/0000-0001-7002-6730)
- Elias Picazo (ORCID: https://orcid.org/0000-0001-5153-4131)
- Eric N. Jacobsen (ORCID: https://orcid.org/0000-0001-7952-3661)
- Michael Martin Nielsen (ORCID: https://orcid.org/0000-0003-2408-9217)
Institutions
- Harvard University (US)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-09-30
- DOI
- https://doi.org/10.1021/jacs.4c11560
- Citations
- 18
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 4.50
Funders
- Harvard University
- Mizutani Foundation for Glycoscience
- Danmarks Frie Forskningsfond
- National Institutes of Health
- National Institute of General Medical Sciences