Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 142, Issue 27, Pages 11865-11872Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.0c04255
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- NIH [GM132571]
- NSF
- Common Fund Glycoscience Program [U01 GM116249]
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We report highly beta-selective bis-thioureas-catalyzed 1,2-cis-O-pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles, including complex natural products, glycosides, and amino acids were beta-mannosylated and beta-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high beta-selectivities.
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