期刊
ORGANIC LETTERS
卷 23, 期 15, 页码 5636-5640出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01713
关键词
-
资金
- National Institute of General Medical Science of the National Institutes of Health [R01GM130693]
- [CHE-1828183]
A variety of C-glycosides can be synthesized through a one-step functionalization process by changing the addition order, Lewis acid, and TMS-X, resulting in common C-pyranosides, rare C-furanosides, and virtually unknown anhydro-C-pyranosides. These synthons are obtained through different mechanisms such as direct substitution, isomerization/substitution, or substitution/isomerization.
A variety of C-glycosides can be obtained from the fluoroarylborane (B(C6F5)(3)) or silylium (R3Si+) catalyzed functionalization of 1-MeO- and per-TMS-sugars with TMS-X reagents. A one-step functionalization with a change as simple as the addition order and/or Lewis acid and TMS-X enables one to afford chiral synthons that are common (C-pyranosides), have few viable synthetic methods (C-furanosides), or are virtually unknown (anhydro-C-pyranosides), which mechanistically arise from whether a direct substitution, isomerization/substitution, or substitution/isomerization occurs, respectively.
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