Modular and Stereoselective Synthesis of C‑Aryl Glycosides via Catellani Reaction

In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)­aryl glycosides in a modular and stereoselective manner (>90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuk...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 142; no. 35; pp. 14864 - 14870
Main Authors Lv, Weiwei, Chen, Yanhui, Wen, Si, Ba, Dan, Cheng, Guolin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.09.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
GLYCOSYLATION REACTIONS
H FUNCTIONALIZATION
ORTHO-ALKYLATION
ACTIVATION
CANAGLIFLOZIN
ANNULATION
ARYLATION
INHIBITOR
PD/NORBORNENE
DISCOVERY
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Summary:In this work, we describe a Catellani-type C–H glycosylation to provide rapid access to various highly decorated α-C-(hetero)­aryl glycosides in a modular and stereoselective manner (>90 examples). The termination step is flexible, which is demonstrated by ipso-Heck reaction, hydrogenation, Suzuki coupling, and Sonogashira coupling. Application of this methodology has been showcased by preparing glycoside–pharmacophore conjugates and a dapagliflozin analogue. Notably, the technology developed herein represents an unprecedented example of Catellani-type alkylation involving an SN1 pathway.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c07634