CN

Diversity-oriented synthesis of fused thioglycosyl benzo[e][1,4]oxathiepin-5-ones and benzo[f][1,4]thiazepin-5(2H)-ones by a sequence of palladium-catalyzed glycosyl thiol arylation and deprotection-lactonization reactions.

Diversity-oriented synthesis of fused thioglycosyl benzo[e][1,4]oxathiepin-5-ones and benzo[f][1,4]thiazepin-5(2H)-ones by a sequence of palladium-catalyzed glycosyl thiol arylation and deprotection-lactonization reactions.

Organic & biomolecular chemistry (2015-09-16)

Riyadh Ahmed Atto AL-Shuaeeb, Gilles Galvani, Guillaume Bernadat, Jean-Daniel Brion, Mouad Alami, Samir Messaoudi

摘要

An efficient synthesis of thioglycosylated benzo[e][1,4]oxathiepin-5-one and benzothiazepinone derivatives by a sequence of palladium-catalyzed glycosyl thiol arylation followed by deprotection-lactonization reactions has been reported. This diversity-oriented strategy enabled access to unknown complex cyclic scaffolds with polyhydroxylated appendages of biological interest.

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二甲基亚砜-d ₆, 99.9 atom % D

Sigma-Aldrich

氯仿-d, 99.8 atom % D

Sigma-Aldrich

乙酸乙酯, ACS reagent, ≥99.5%

Sigma-Aldrich

二甲基亚砜-d ₆, 99.9 atom % D, contains 0.03 % (v/v) TMS

Sigma-Aldrich

氯仿-d, 99.8 atom % D, contains 0.03 % (v/v) TMS

Sigma-Aldrich

乙酸乙酯, anhydrous, 99.8%

Sigma-Aldrich

碳酸钾, ACS reagent, ≥99.0%

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二甲基亚砜-d ₆, 99.5 atom % D

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环己烷, ACS reagent, ≥99%

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环己烷, anhydrous, 99.5%

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碳酸钾, anhydrous, free-flowing, Redi-Dri^™, ACS reagent, ≥99%

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乙酸乙酯, puriss., meets analytical specification of Ph. Eur., BP, NF, ≥99.5% (GC)

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碳酸钾, reagent grade, ≥98%, powder, −325 mesh

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二甲基亚砜-d ₆, "100%", 99.96 atom % D

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氯仿-d, 99.8 atom % D, contains 0.05 % (v/v) TMS

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氯仿-d, 99.8 atom % D, contains 0.1 % (v/v) TMS

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环己烷, Laboratory Reagent, ≥99.8%

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乙酸乙酯, puriss. p.a., ACS reagent, reag. ISO, reag. Ph. Eur., ≥99.5% (GC)

Sigma-Aldrich

氯仿-d, 99.8 atom % D, contains 1 % (v/v) TMS

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碳酸钾, 99.995% trace metals basis

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环己烷, puriss. p.a., ACS reagent, ≥99.5% (GC)

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氯仿-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS

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碳酸钾, puriss. p.a., ACS reagent, anhydrous, ≥99.0% (T)

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碳酸钾, anhydrous, powder, 99.99% trace metals basis

Sigma-Aldrich

二甲基亚砜-d ₆, 99.9 atom % D, contains 1 % (v/v) TMS

Sigma-Aldrich

二甲基亚砜-d ₆, anhydrous, 99.9 atom % D

Sigma-Aldrich

氯仿-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer

Sigma-Aldrich

氯仿-d, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS

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碳酸钾, BioXtra, ≥99.0%

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乙酸乙酯, ≥99%, FCC, FG