2004
DOI: 10.1002/chin.200441193
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Synthesis of C‐Aryl‐Δ2,3‐glycopyranosides via Uncatalyzed Addition of Triarylindium Reagents to Glycals.

Abstract: Synthesis of C-Aryl-∆ 2,3 -glycopyranosides via Uncatalyzed Addition of Triarylindium Reagents to Glycals. -The title reaction produces glycopyranosides in good yields and diastereoselectivity. The method can be extended to trivinyl-and tris(alkynyl)indiums with similar results. -(PRICE, S.; EDWARDS, S.; WU, T.; MINEHAN*, T.; Tetrahedron Lett. 45 (2004) 27, 5197-5201; Dep. Chem., Harvey Mudd Coll., Claremont, CA 91711, USA; Eng.) -Mais 41-193

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“…232 The Lewis acid character of organoindium compounds has also been exploited to get 2,3-unsaturated C-glycosyl arenes 204 by using triaryl indiums (Scheme 37, route b also with D-galactal, D-allal, and L-rhamnal besides 85). 233 All three aryl groups participated in the reaction because substoichiometric amounts of triaryl indium delivered the corresponding products 204 in high yields (e.g., 86% with 0.33 equiv of InPh 3 ), while the stereoselectivity strongly depended on the sugar configuration (e.g., α/β 1 to 6:1 for D-glucal and L-rhamnal, 10:1 for D-galactal).…”
Section: Sugar Chain Closure Methods Toward C-glycosyl Arenesmentioning
confidence: 99%
“…232 The Lewis acid character of organoindium compounds has also been exploited to get 2,3-unsaturated C-glycosyl arenes 204 by using triaryl indiums (Scheme 37, route b also with D-galactal, D-allal, and L-rhamnal besides 85). 233 All three aryl groups participated in the reaction because substoichiometric amounts of triaryl indium delivered the corresponding products 204 in high yields (e.g., 86% with 0.33 equiv of InPh 3 ), while the stereoselectivity strongly depended on the sugar configuration (e.g., α/β 1 to 6:1 for D-glucal and L-rhamnal, 10:1 for D-galactal).…”
Section: Sugar Chain Closure Methods Toward C-glycosyl Arenesmentioning
confidence: 99%