Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid: Stereoselective synthesis of glycosides and 2-deoxyglycosides

Monika Poláková; Nigel Pitt; Manuela Tosin; Paul V. Murphy

doi:10.1002/anie.200353196

Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid: Stereoselective synthesis of glycosides and 2-deoxyglycosides

Monika Poláková
, Nigel Pitt
, Manuela Tosin
, Paul V. Murphy

University College Dublin

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

58 Citations (Scopus)

Abstract

The donor makes the difference: The tin(IV) chloride catalyzed coupling of silyl ethers to donors derived from glucuronic acid has shown that the silyl ethers (see scheme) are significantly better acceptors than the corresponding alcohols or phenol. The reactions are highly stereoselective and dependant on the donor structure. They provide 1,2-trans- and 1,2-cis-(deoxy)glycosides in moderate to excellent yields.

Original language	English
Pages (from-to)	2518-2521
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	19
DOIs	https://doi.org/10.1002/anie.200353196
Publication status	Published - 3 May 2004
Externally published	Yes

Keywords

Carbohydrates
Glucuronic acid
Glycosides
Glycosylation
Stereoselective synthesis

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10.1002/anie.200353196

Cite this

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title = "Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid: Stereoselective synthesis of glycosides and 2-deoxyglycosides",

abstract = "The donor makes the difference: The tin(IV) chloride catalyzed coupling of silyl ethers to donors derived from glucuronic acid has shown that the silyl ethers (see scheme) are significantly better acceptors than the corresponding alcohols or phenol. The reactions are highly stereoselective and dependant on the donor structure. They provide 1,2-trans- and 1,2-cis-(deoxy)glycosides in moderate to excellent yields.",

keywords = "Carbohydrates, Glucuronic acid, Glycosides, Glycosylation, Stereoselective synthesis",

author = "Monika Pol{\'a}kov{\'a} and Nigel Pitt and Manuela Tosin and Murphy, \{Paul V.\}",

year = "2004",

month = may,

day = "3",

doi = "10.1002/anie.200353196",

language = "English",

volume = "43",

pages = "2518--2521",

journal = "Angewandte Chemie - International Edition",

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Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid: Stereoselective synthesis of glycosides and 2-deoxyglycosides. / Poláková, Monika; Pitt, Nigel; Tosin, Manuela et al.
In: Angewandte Chemie - International Edition, Vol. 43, No. 19, 03.05.2004, p. 2518-2521.

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

TY - JOUR

T1 - Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid

T2 - Stereoselective synthesis of glycosides and 2-deoxyglycosides

AU - Poláková, Monika

AU - Pitt, Nigel

AU - Tosin, Manuela

AU - Murphy, Paul V.

PY - 2004/5/3

Y1 - 2004/5/3

N2 - The donor makes the difference: The tin(IV) chloride catalyzed coupling of silyl ethers to donors derived from glucuronic acid has shown that the silyl ethers (see scheme) are significantly better acceptors than the corresponding alcohols or phenol. The reactions are highly stereoselective and dependant on the donor structure. They provide 1,2-trans- and 1,2-cis-(deoxy)glycosides in moderate to excellent yields.

AB - The donor makes the difference: The tin(IV) chloride catalyzed coupling of silyl ethers to donors derived from glucuronic acid has shown that the silyl ethers (see scheme) are significantly better acceptors than the corresponding alcohols or phenol. The reactions are highly stereoselective and dependant on the donor structure. They provide 1,2-trans- and 1,2-cis-(deoxy)glycosides in moderate to excellent yields.

KW - Carbohydrates

KW - Glucuronic acid

KW - Glycosides

KW - Glycosylation

KW - Stereoselective synthesis

UR - https://www.scopus.com/pages/publications/3342915857

U2 - 10.1002/anie.200353196

DO - 10.1002/anie.200353196

M3 - Article

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JF - Angewandte Chemie - International Edition

IS - 19

ER -

Glycosidation reactions of silyl ethers with conformationally inverted donors derived from glucuronic acid: Stereoselective synthesis of glycosides and 2-deoxyglycosides

Abstract

Keywords

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