Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)₄ and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

Peiran Chen,Saisai Guo, Junfeng Zuo, Ruiji Chu,Xu He, Guijiang Zhu

TETRAHEDRON LETTERS（2020）

Cited 6|Views9

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Abstract

By using Hf(OTf)(4) as the catalyst, under certain conditions, reaction of tri-O-acetyl-D-glucal and ((2R,3S)-3-acetoxy-2,3-dihydrofuran-2-yl)methyl acetate with alkyl(aryl) bisulfide/alkyl(aryl) biselenide as nucleophile precursor leads to temperature-dependent formation of C-1-S/Se and C-3-S/Se product. A temperature-dependent profile of the yield of these two products is given. (C) 2020 Elsevier Ltd. All rights reserved.

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Key words

Hf(OTf)(4),(RS)(2)/(RSe)(2),C-1-S/Se,C-3-S/Se glycal,Ferrier Rearrangement

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Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)4 and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products

Synthesis of 3-S- and 3-Se-glycals by using R-S-S-R and R-Se-Se-R as the nucleophile precursors promoted by Hf(OTf)₄ and the temperature-dependent formation of the above-mentioned 3-S- and 3-Se products