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  • 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
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Cyclohexane, SAJ first grade, ≥99.0%
Sigma-Aldrich
Cyclohexane, JIS special grade
Sigma-Aldrich
Cyclohexane, suitable for HPLC
Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer
Sigma-Aldrich
Cyclohexane, anhydrous, 99.5%
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.9 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, contains 0.5 wt. % silver foil as stabilizer, 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.1 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.03 % (v/v) TMS
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.9 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.9 atom % D
Sigma-Aldrich
Dimethyl sulfoxide-d6, 99.5 atom % D
Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D
Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Chloroform-d, 99.8 atom % D
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 1 % (v/v) TMS
Sigma-Aldrich
Chloroform-d, ≥99.8 atom % D, anhydrous
Sigma-Aldrich
Dimethyl sulfoxide-d6, anhydrous, 99.9 atom % D
Sigma-Aldrich
Chloroform-d, 99.8 atom % D, contains 0.05 % (v/v) TMS
Sigma-Aldrich
Cyclohexane, Laboratory Reagent, ≥99.8%
Sigma-Aldrich
Cyclohexane, puriss. p.a., ACS reagent, ≥99.5% (GC)
Sigma-Aldrich
Cyclohexane, ACS reagent, ≥99%
Sigma-Aldrich
Cyclohexane, ACS reagent, ≥99%
Sigma-Aldrich
Chloroform-d, "100%", 99.96 atom % D, contains 0.5 wt. % silver wire as stabilizer
Sigma-Aldrich
Dimethyl sulfoxide-d6, "100%", 99.96 atom % D
Sigma-Aldrich
Potassium carbonate, anhydrous, powder, 99.99% trace metals basis
Sigma-Aldrich
Ethyl acetate, JIS 1000, ≥99.5%, for residue analysis