Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

Sandra Medina Villar; Matt Harper; Edward Balmond; Silvia Miranda Alcazar; Giacomo Crisenza; Diane M Coe; Eoghan M. McGarrigle; Carmen Galan

doi:10.1021/acs.orglett.6b01962

Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

Sandra Medina Villar, Matt Harper, Edward Balmond, Silvia Miranda Alcazar, Giacomo Crisenza, Diane M Coe, Eoghan M. McGarrigle, Carmen Galan

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

63 Citations (Scopus)

712 Downloads (Pure)

Abstract

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

Original language	English
Pages (from-to)	4222-4225
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	17
Early online date	16 Aug 2016
DOIs	https://doi.org/10.1021/acs.orglett.6b01962
Publication status	Published - 2 Sept 2016

Research Groups and Themes

BCS and TECS CDTs
Organic & Biological

Access to Document

10.1021/acs.orglett.6b01962

Full-text PDF (accepted author manuscript)
This is the accepted author manuscript (AAM). The final published version (version of record) is available online via American Chemical Society at http://dx.doi.org/10.1021/acs.orglett.6b01962. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 478 KB
Full-text PDF (final published version)
This is the final published version of the article (version of record). It first appeared online via American Chemical Society at http://dx.doi.org/10.1021/acs.orglett.6b01962. Please refer to any applicable terms of use of the publisher.
Final published version, 643 KBLicence: CC BY
Supplementary Information PDF
This is the final published version of the article (version of record). It first appeared online via American Chemical Society at http://dx.doi.org/10.1021/acs.orglett.6b01962. Please refer to any applicable terms of use of the publisher.
Final published version, 5.04 MBLicence: CC BY

Handle.net

Persistent link

Catalytic stereoselective synthesis of glycosides
Galan, M. C. (Principal Investigator)
1/07/13 → 1/07/15
Project: Research
3-month Core Capability for Chemistry Research
Crosby, J. (Principal Investigator)
1/01/13 → 1/04/13
Project: Research
Reworking of Novel tools for Glycoscience
Galan, M. C. (Principal Investigator)
31/03/12 → 30/08/17
Project: Research

Cite this

@article{01c2fd7396724d2d8faf704e1d4f4657,

title = "Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst",

abstract = "The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.",

author = "\{Medina Villar\}, Sandra and Matt Harper and Edward Balmond and \{Miranda Alcazar\}, Silvia and Giacomo Crisenza and Coe, \{Diane M\} and McGarrigle, \{Eoghan M.\} and Carmen Galan",

year = "2016",

month = sep,

day = "2",

doi = "10.1021/acs.orglett.6b01962",

language = "English",

volume = "18",

pages = "4222--4225",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "17",

}

TY - JOUR

T1 - Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

AU - Medina Villar, Sandra

AU - Harper, Matt

AU - Balmond, Edward

AU - Miranda Alcazar, Silvia

AU - Crisenza, Giacomo

AU - Coe, Diane M

AU - McGarrigle, Eoghan M.

AU - Galan, Carmen

PY - 2016/9/2

Y1 - 2016/9/2

N2 - The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

AB - The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

U2 - 10.1021/acs.orglett.6b01962

DO - 10.1021/acs.orglett.6b01962

M3 - Article (Academic Journal)

C2 - 27529800

SN - 1523-7060

VL - 18

SP - 4222

EP - 4225

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

Abstract

Research Groups and Themes

Access to Document

Handle.net

Fingerprint

Projects

Catalytic stereoselective synthesis of glycosides

3-month Core Capability for Chemistry Research

Reworking of Novel tools for Glycoscience

Cite this