A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

Edward I. Balmond; David Benito-Alifonso; Diane M. Coe; Roger W. Alder; Eoghan M. McGarrigle; M. Carmen Galan

doi:10.1002/anie.201403543

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

Edward I. Balmond, David Benito-Alifonso, Diane M. Coe, Roger W. Alder, Eoghan M. McGarrigle, M. Carmen Galan

Research output: Contribution to journal › Article (Academic Journal) › peer-review

105 Citations (Scopus)

Abstract

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H₂O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

Original language	English
Pages (from-to)	8190-8194
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	53
Issue number	31
DOIs	https://doi.org/10.1002/anie.201403543
Publication status	Published - 28 Jul 2014

Research Groups and Themes

BCS and TECS CDTs

Keywords

conformation analysis
glycosides
homogeneous catalysis
protecting groups
synthetic methods

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10.1002/anie.201403543

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Cite this

@article{0bc8f79b3f464093a47751931c8b8fc5,

title = "A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides",

abstract = "A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.",

keywords = "conformation analysis, glycosides, homogeneous catalysis, protecting groups, synthetic methods",

author = "Balmond, {Edward I.} and David Benito-Alifonso and Coe, {Diane M.} and Alder, {Roger W.} and McGarrigle, {Eoghan M.} and Galan, {M. Carmen}",

year = "2014",

month = jul,

day = "28",

doi = "10.1002/anie.201403543",

language = "English",

volume = "53",

pages = "8190--8194",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "Wiley-VCH Verlag",

number = "31",

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TY - JOUR

T1 - A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

AU - Balmond, Edward I.

AU - Benito-Alifonso, David

AU - Coe, Diane M.

AU - Alder, Roger W.

AU - McGarrigle, Eoghan M.

AU - Galan, M. Carmen

PY - 2014/7/28

Y1 - 2014/7/28

N2 - A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

AB - A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.

KW - conformation analysis

KW - glycosides

KW - homogeneous catalysis

KW - protecting groups

KW - synthetic methods

UR - http://www.scopus.com/inward/record.url?scp=84905403688&partnerID=8YFLogxK

U2 - 10.1002/anie.201403543

DO - 10.1002/anie.201403543

M3 - Article (Academic Journal)

C2 - 24953049

AN - SCOPUS:84905403688

SN - 1433-7851

VL - 53

SP - 8190

EP - 8194

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 31

ER -

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Catalytic stereoselective synthesis of glycosides

3-month Core Capability for Chemistry Research

Reworking of Novel tools for Glycoscience

Professor M C Galan

Cite this

A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides

Abstract

Research Groups and Themes

Keywords

Access to Document

Handle.net

Other files and links

Fingerprint

Projects

Catalytic stereoselective synthesis of glycosides

3-month Core Capability for Chemistry Research

Reworking of Novel tools for Glycoscience

Profiles

Professor M C Galan

Cite this