AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives

Robin Jeanneret; Carlo Walz; Maarten van Meerbeek; Sarah Coppock; M Carmen Galan

doi:10.1021/acs.orglett.2c02530

AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives

Robin Jeanneret, Carlo Walz, Maarten van Meerbeek, Sarah Coppock, M Carmen Galan

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Abstract

A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α'-linked 2-deoxy trehalose analogues via AuCl 3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.

Original language	English
Pages (from-to)	6304-6309
Number of pages	6
Journal	Organic Letters
Volume	24
Issue number	34
DOIs	https://doi.org/10.1021/acs.orglett.2c02530
Publication status	Published - 2 Sept 2022

Bibliographical note

Funding Information:
M.C.G. thanks the European Research Council (ERC-COG, 648239) and EPSRC GCRF EP/T020288/1 and EP/S026215/1.

Publisher Copyright:
© 2022 The Authors. Published by American Chemical Society.

Research Groups and Themes

BCS and TECS CDTs

Keywords

Catalysis
Glycosylation
Stereoisomerism
Trehalose

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10.1021/acs.orglett.2c02530

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@article{b409b318e5254772af3055bad5bd55af,

title = "AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives",

abstract = "A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α'-linked 2-deoxy trehalose analogues via AuCl 3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Br{\o}nsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals. ",

keywords = "Catalysis, Glycosylation, Stereoisomerism, Trehalose",

author = "Robin Jeanneret and Carlo Walz and {van Meerbeek}, Maarten and Sarah Coppock and Galan, {M Carmen}",

note = "Funding Information: M.C.G. thanks the European Research Council (ERC-COG, 648239) and EPSRC GCRF EP/T020288/1 and EP/S026215/1. Publisher Copyright: {\textcopyright} 2022 The Authors. Published by American Chemical Society.",

year = "2022",

month = sep,

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doi = "10.1021/acs.orglett.2c02530",

language = "English",

volume = "24",

pages = "6304--6309",

journal = "Organic Letters",

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TY - JOUR

T1 - AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives

AU - Jeanneret, Robin

AU - Walz, Carlo

AU - van Meerbeek, Maarten

AU - Coppock, Sarah

AU - Galan, M Carmen

N1 - Funding Information: M.C.G. thanks the European Research Council (ERC-COG, 648239) and EPSRC GCRF EP/T020288/1 and EP/S026215/1. Publisher Copyright: © 2022 The Authors. Published by American Chemical Society.

PY - 2022/9/2

Y1 - 2022/9/2

N2 - A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α'-linked 2-deoxy trehalose analogues via AuCl 3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.

AB - A new practical, catalytic, and highly stereoselective method for directly accessing 1,1-α,α'-linked 2-deoxy trehalose analogues via AuCl 3-catalyzed dehydrative glycosylation using hemiacetal glycosyl donors and acceptors is described. The method relies on the chemoselective Brønsted acid-type activation of tribenzylated 2-deoxy hemiacetals in the presence of other less reactive hemiacetals.

KW - Catalysis

KW - Glycosylation

KW - Stereoisomerism

KW - Trehalose

U2 - 10.1021/acs.orglett.2c02530

DO - 10.1021/acs.orglett.2c02530

M3 - Article (Academic Journal)

C2 - 35994370

SN - 1523-7060

VL - 24

SP - 6304

EP - 6309

JO - Organic Letters

JF - Organic Letters

IS - 34

ER -

AuCl3-Catalyzed Hemiacetal Activation for the Stereoselective Synthesis of 2-Deoxy Trehalose Derivatives

Abstract

Bibliographical note

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Keywords

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