Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts

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Standard

Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts. / Yang, Liang; Hammelev, Christian Herrstedt; Pedersen, Christian Marcus.

I: ChemSusChem, Bind 13, Nr. 12, 2020, s. 3166-3171.

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt

Harvard

Yang, L, Hammelev, CH & Pedersen, CM 2020, 'Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts', ChemSusChem, bind 13, nr. 12, s. 3166-3171. https://doi.org/10.1002/cssc.202000733

APA

Yang, L., Hammelev, C. H., & Pedersen, C. M. (2020). Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts. ChemSusChem, 13(12), 3166-3171. https://doi.org/10.1002/cssc.202000733

Vancouver

Yang L, Hammelev CH, Pedersen CM. Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts. ChemSusChem. 2020;13(12):3166-3171. https://doi.org/10.1002/cssc.202000733

Author

Yang, Liang ; Hammelev, Christian Herrstedt ; Pedersen, Christian Marcus. / Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts. I: ChemSusChem. 2020 ; Bind 13, Nr. 12. s. 3166-3171.

Bibtex

@article{0c4daabd4c244e26b3859319a5c67681,
title = "Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts",
abstract = "Benzylated glycosyl formates have been synthesized in one step from the corresponding hemiacetal or orthoester with formic acid as the sole reagent. The glycosyl formates are used as glycosyl donors under catalytic conditions with cheap metal catalysts based on iron or bismuth. A 13C NMR spectroscopic method is developed and evaluated for screening reactions conditions, giving precise information on the selectivity, yield, and byproducts formed. The major side reaction is transesterification, which gives the formylated acceptor and regenerates the hemiacetal. By using this approach, catalyst loadings and solvents are optimized and the scope of the glycosylation is evaluated for a variety of glycosyl donors and acceptors. A proof of concept for a traceless glycosylation, utilizing a dual‐purpose iron catalyst that catalyzes both glycosylation and dehydrogenation of formic acid, is also provided.",
author = "Liang Yang and Hammelev, {Christian Herrstedt} and Pedersen, {Christian Marcus}",
year = "2020",
doi = "10.1002/cssc.202000733",
language = "English",
volume = "13",
pages = "3166--3171",
journal = "ChemSusChem",
issn = "1864-5631",
publisher = "Chemistry Europe - European Chemical Societies Publishing",
number = "12",

}

RIS

TY - JOUR

T1 - Catalytic and Atom Economic Glycosylation using Glycosyl Formates and Cheap Metal Salts

AU - Yang, Liang

AU - Hammelev, Christian Herrstedt

AU - Pedersen, Christian Marcus

PY - 2020

Y1 - 2020

N2 - Benzylated glycosyl formates have been synthesized in one step from the corresponding hemiacetal or orthoester with formic acid as the sole reagent. The glycosyl formates are used as glycosyl donors under catalytic conditions with cheap metal catalysts based on iron or bismuth. A 13C NMR spectroscopic method is developed and evaluated for screening reactions conditions, giving precise information on the selectivity, yield, and byproducts formed. The major side reaction is transesterification, which gives the formylated acceptor and regenerates the hemiacetal. By using this approach, catalyst loadings and solvents are optimized and the scope of the glycosylation is evaluated for a variety of glycosyl donors and acceptors. A proof of concept for a traceless glycosylation, utilizing a dual‐purpose iron catalyst that catalyzes both glycosylation and dehydrogenation of formic acid, is also provided.

AB - Benzylated glycosyl formates have been synthesized in one step from the corresponding hemiacetal or orthoester with formic acid as the sole reagent. The glycosyl formates are used as glycosyl donors under catalytic conditions with cheap metal catalysts based on iron or bismuth. A 13C NMR spectroscopic method is developed and evaluated for screening reactions conditions, giving precise information on the selectivity, yield, and byproducts formed. The major side reaction is transesterification, which gives the formylated acceptor and regenerates the hemiacetal. By using this approach, catalyst loadings and solvents are optimized and the scope of the glycosylation is evaluated for a variety of glycosyl donors and acceptors. A proof of concept for a traceless glycosylation, utilizing a dual‐purpose iron catalyst that catalyzes both glycosylation and dehydrogenation of formic acid, is also provided.

U2 - 10.1002/cssc.202000733

DO - 10.1002/cssc.202000733

M3 - Journal article

C2 - 32267068

VL - 13

SP - 3166

EP - 3171

JO - ChemSusChem

JF - ChemSusChem

SN - 1864-5631

IS - 12

ER -

ID: 240148562