Practical Site-Selective Oxidation of Glycosides with Palladium(II) 
Acetate/Neocuproine

Niels R. M. Reintjens; Imke M. A.  Bartels; Nittert Marinus; Sarina C. Massmann; Daan V. Bunt; Marthe T. C. Walvoort; Martin D. Witte; Adriaan J. Minnaard

doi:10.1055/a-2186-1485

Practical Site-Selective Oxidation of Glycosides with Palladium(II) Acetate/Neocuproine

Niels R. M. Reintjens, Imke M. A. Bartels, Nittert Marinus, Sarina C. Massmann, Daan V. Bunt, Marthe T. C. Walvoort, Martin D. Witte^*, Adriaan J. Minnaard^*

^*Corresponding author voor dit werk

Bio-organic Chemistry

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The palladium-catalyzed oxidation of the secondary C(3) hydroxy group of glycopyranosides has set a mark in the selective modification of unprotected carbohydrates. The preformed catalyst [(neocuproine)PdOAc]₂(OTf)₂ oxidizes di- and oligosaccharides, as well as monosaccharides. Here, we provide a more convenient protocol for this reaction in which the Pd catalyst is formed in situ from Pd(OAc)₂ and neocuproine in methanol at 50 °C. Together with a simplified product isolation, this protocol was applied to a series of mono- and disaccharides, and has been applied on a 10 gram scale. The protocol is also valuable as a screening method to determine whether more-extensive studies using the preformed catalyst are worthwhile.

Originele taal-2	English
Artikelnummer	a-2186-1485
Pagina's (van-tot)	1291-1295
Aantal pagina's	5
Tijdschrift	Synlett
Volume	35
Nummer van het tijdschrift	11
Vroegere onlinedatum	9-nov.-2023
DOI's	https://doi.org/10.1055/a-2186-1485
Status	Published - 2-jul.-2024

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title = "Practical Site-Selective Oxidation of Glycosides with Palladium(II) Acetate/Neocuproine",

abstract = "The palladium-catalyzed oxidation of the secondary C(3) hydroxy group of glycopyranosides has set a mark in the selective modification of unprotected carbohydrates. The preformed catalyst [(neocuproine)PdOAc]2(OTf)2 oxidizes di- and oligosaccharides, as well as monosaccharides. Here, we provide a more convenient protocol for this reaction in which the Pd catalyst is formed in situ from Pd(OAc)2 and neocuproine in methanol at 50 °C. Together with a simplified product isolation, this protocol was applied to a series of mono- and disaccharides, and has been applied on a 10 gram scale. The protocol is also valuable as a screening method to determine whether more-extensive studies using the preformed catalyst are worthwhile.",

keywords = "glycosides, oxidation, palladium catalysis, neocuproine, site-selectivity, regioselectivity",

author = "Reintjens, {Niels R. M.} and Bartels, {Imke M. A.} and Nittert Marinus and Massmann, {Sarina C.} and Bunt, {Daan V.} and Walvoort, {Marthe T. C.} and Witte, {Martin D.} and Minnaard, {Adriaan J.}",

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T1 - Practical Site-Selective Oxidation of Glycosides with Palladium(II) Acetate/Neocuproine

AU - Reintjens, Niels R. M.

AU - Bartels, Imke M. A.

AU - Marinus, Nittert

AU - Massmann, Sarina C.

AU - Bunt, Daan V.

AU - Walvoort, Marthe T. C.

AU - Witte, Martin D.

AU - Minnaard, Adriaan J.

PY - 2024/7/2

Y1 - 2024/7/2

N2 - The palladium-catalyzed oxidation of the secondary C(3) hydroxy group of glycopyranosides has set a mark in the selective modification of unprotected carbohydrates. The preformed catalyst [(neocuproine)PdOAc]2(OTf)2 oxidizes di- and oligosaccharides, as well as monosaccharides. Here, we provide a more convenient protocol for this reaction in which the Pd catalyst is formed in situ from Pd(OAc)2 and neocuproine in methanol at 50 °C. Together with a simplified product isolation, this protocol was applied to a series of mono- and disaccharides, and has been applied on a 10 gram scale. The protocol is also valuable as a screening method to determine whether more-extensive studies using the preformed catalyst are worthwhile.

AB - The palladium-catalyzed oxidation of the secondary C(3) hydroxy group of glycopyranosides has set a mark in the selective modification of unprotected carbohydrates. The preformed catalyst [(neocuproine)PdOAc]2(OTf)2 oxidizes di- and oligosaccharides, as well as monosaccharides. Here, we provide a more convenient protocol for this reaction in which the Pd catalyst is formed in situ from Pd(OAc)2 and neocuproine in methanol at 50 °C. Together with a simplified product isolation, this protocol was applied to a series of mono- and disaccharides, and has been applied on a 10 gram scale. The protocol is also valuable as a screening method to determine whether more-extensive studies using the preformed catalyst are worthwhile.

KW - glycosides

KW - oxidation

KW - palladium catalysis

KW - neocuproine

KW - site-selectivity

KW - regioselectivity

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