Metal-mediated allylation of enzymatically oxidized methyl alpha-D-galactopyranoside

Ann-Sofie Leppänen; Outi Niittymäki; Kirsti Parikka; Maija Tenkanen; Patrik Christoffer Eklund; Rainer Sjöholm; Stefan Willför

doi:10.1016/j.carres.2010.09.026

Metal-mediated allylation of enzymatically oxidized methyl alpha-D-galactopyranoside

Ann-Sofie Leppänen, Outi Niittymäki, Kirsti Parikka, Maija Tenkanen, Patrik Christoffer Eklund, Rainer Sjöholm, Stefan Willför

Research output: Contribution to journal › Article › Scientific › peer-review

14 Citations (Scopus)

Abstract

The C-6 unit of methyl alpha-D-galactopyranoside was selectively modified by combining enzymatic oxidation with an indium-mediated allylation reaction The Barbier-Grignard type reaction where a carbonyl group reacts with an allyl halide proceeds in aqueous solution even with water as the only solvent thus carbohydrates can be modified without the need for drying or protection-deprotection steps The corresponding homoallyl alcohols are produced in high yields of >90% in the reactions with allyl bromide and cinnamyl chloride The main products were Isolated and characterized by GC-MS and NMR spectroscopy (C) 2010 Elsevier Ltd All rights reserved

Original language	Undefined/Unknown
Pages (from-to)	2610–2615
Number of pages	6
Journal	Carbohydrate Research
Volume	345
Issue number	18
DOIs	https://doi.org/10.1016/j.carres.2010.09.026
Publication status	Published - 2010
MoE publication type	A1 Journal article-refereed

Keywords

Allylation
Aqueous media
Indium mediated
Methyl alpha-D-galactopyranoside

Access to Document

10.1016/j.carres.2010.09.026

Cite this

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title = "Metal-mediated allylation of enzymatically oxidized methyl alpha-D-galactopyranoside",

abstract = "The C-6 unit of methyl alpha-D-galactopyranoside was selectively modified by combining enzymatic oxidation with an indium-mediated allylation reaction The Barbier-Grignard type reaction where a carbonyl group reacts with an allyl halide proceeds in aqueous solution even with water as the only solvent thus carbohydrates can be modified without the need for drying or protection-deprotection steps The corresponding homoallyl alcohols are produced in high yields of >90\% in the reactions with allyl bromide and cinnamyl chloride The main products were Isolated and characterized by GC-MS and NMR spectroscopy (C) 2010 Elsevier Ltd All rights reserved",

keywords = "Allylation, Aqueous media, Indium mediated, Methyl alpha-D-galactopyranoside, Allylation, Aqueous media, Indium mediated, Methyl alpha-D-galactopyranoside, Allylation, Aqueous media, Indium mediated, Methyl alpha-D-galactopyranoside",

author = "Ann-Sofie Lepp{\"a}nen and Outi Niittym{\"a}ki and Kirsti Parikka and Maija Tenkanen and Eklund, \{Patrik Christoffer\} and Rainer Sj{\"o}holm and Stefan Willf{\"o}r",

year = "2010",

doi = "10.1016/j.carres.2010.09.026",

language = "Odefinierat/ok{\"a}nt",

volume = "345",

pages = "2610–2615",

journal = "Carbohydrate Research",

issn = "0008-6215",

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T1 - Metal-mediated allylation of enzymatically oxidized methyl alpha-D-galactopyranoside

AU - Leppänen, Ann-Sofie

AU - Niittymäki, Outi

AU - Parikka, Kirsti

AU - Tenkanen, Maija

AU - Eklund, Patrik Christoffer

AU - Sjöholm, Rainer

AU - Willför, Stefan

PY - 2010

Y1 - 2010

N2 - The C-6 unit of methyl alpha-D-galactopyranoside was selectively modified by combining enzymatic oxidation with an indium-mediated allylation reaction The Barbier-Grignard type reaction where a carbonyl group reacts with an allyl halide proceeds in aqueous solution even with water as the only solvent thus carbohydrates can be modified without the need for drying or protection-deprotection steps The corresponding homoallyl alcohols are produced in high yields of >90% in the reactions with allyl bromide and cinnamyl chloride The main products were Isolated and characterized by GC-MS and NMR spectroscopy (C) 2010 Elsevier Ltd All rights reserved

AB - The C-6 unit of methyl alpha-D-galactopyranoside was selectively modified by combining enzymatic oxidation with an indium-mediated allylation reaction The Barbier-Grignard type reaction where a carbonyl group reacts with an allyl halide proceeds in aqueous solution even with water as the only solvent thus carbohydrates can be modified without the need for drying or protection-deprotection steps The corresponding homoallyl alcohols are produced in high yields of >90% in the reactions with allyl bromide and cinnamyl chloride The main products were Isolated and characterized by GC-MS and NMR spectroscopy (C) 2010 Elsevier Ltd All rights reserved

KW - Allylation

KW - Aqueous media

KW - Indium mediated

KW - Methyl alpha-D-galactopyranoside

KW - Allylation

KW - Aqueous media

KW - Indium mediated

KW - Methyl alpha-D-galactopyranoside

KW - Allylation

KW - Aqueous media

KW - Indium mediated

KW - Methyl alpha-D-galactopyranoside

U2 - 10.1016/j.carres.2010.09.026

DO - 10.1016/j.carres.2010.09.026

M3 - Artikel

SN - 0008-6215

VL - 345

SP - 2610

EP - 2615

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 18

ER -