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binol-derived phosphoric acid catalysts  (Toshima Manufacturing Co Ltd)

 
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    Toshima Manufacturing Co Ltd binol-derived phosphoric acid catalysts
    Binol Derived Phosphoric Acid Catalysts, supplied by Toshima Manufacturing Co Ltd, used in various techniques. Bioz Stars score: 90/100, based on 1 PubMed citations. ZERO BIAS - scores, article reviews, protocol conditions and more
    https://www.bioz.com/product/binol-derived+phosphoric+acid+catalysts/binol+derived+phosphoric+acid+catalysts/10__1021_slash_acs__chemrev__8b00083-252-110-162
    Average 90 stars, based on 1 article reviews
    binol-derived phosphoric acid catalysts - by Bioz Stars, 2026-09
    90/100 stars

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    Activation Assay:

    Article Title: The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface
    Article Snippet: .. Also noteworthy in this respect is Mayr’s observation that DMSO is a significantly stronger nucleophile toward benzyhydryl cations than water or ordinary alcohols.1 This clearly points to the intervention of the reagent as nucleophile in systems activated by combinations of sulfoxides and triflic anhydride, and consequently of glycosyloxy sulfonium ions as intermediates even when the activation is conducted in the presence of the acceptor alcohol.177,239 A number of studies have focused on the use of chiral phosphoric acids, either alone or in combination with thioureas and other additives, as promoters of glycosylation reactions, and the field has been reviewed.240,241 Fairbanks and co-workers were the first to describe the use of binol-derived phosphoric acid catalysts for the activation of a per-O-benzyl-α-D-galactopyranosyl trichloroacetimidate; significant changes in anomeric selectivity were observed as a function of the chirality of the catalyst pointing to the inclusion of the phosphate in the product determining step of the reaction (Scheme 45).242 In related work with a per-O-benzyl-α-D-glucopyranosyl trichloroacetimidate donor, Toshima and co-workers demonstrated that the anomeric selectivity of the reaction was a function of the combination of the absolute configuration of both the binol-derived phosphoric acid catalyst and the simple racemic alcohols employed as acceptors, the later enabling kinetic resolution of the acceptor. ..

    Glycoproteomics:

    Article Title: The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface
    Article Snippet: .. Also noteworthy in this respect is Mayr’s observation that DMSO is a significantly stronger nucleophile toward benzyhydryl cations than water or ordinary alcohols.1 This clearly points to the intervention of the reagent as nucleophile in systems activated by combinations of sulfoxides and triflic anhydride, and consequently of glycosyloxy sulfonium ions as intermediates even when the activation is conducted in the presence of the acceptor alcohol.177,239 A number of studies have focused on the use of chiral phosphoric acids, either alone or in combination with thioureas and other additives, as promoters of glycosylation reactions, and the field has been reviewed.240,241 Fairbanks and co-workers were the first to describe the use of binol-derived phosphoric acid catalysts for the activation of a per-O-benzyl-α-D-galactopyranosyl trichloroacetimidate; significant changes in anomeric selectivity were observed as a function of the chirality of the catalyst pointing to the inclusion of the phosphate in the product determining step of the reaction (Scheme 45).242 In related work with a per-O-benzyl-α-D-glucopyranosyl trichloroacetimidate donor, Toshima and co-workers demonstrated that the anomeric selectivity of the reaction was a function of the combination of the absolute configuration of both the binol-derived phosphoric acid catalyst and the simple racemic alcohols employed as acceptors, the later enabling kinetic resolution of the acceptor. ..



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