Hydrogen-bond-mediated aglycone delivery (HAD) and related methods in carbohydrate chemistry

Michael P. Mannino; Alexei Demchenko

doi:10.1039/9781788013864-00093

Hydrogen-bond-mediated aglycone delivery (HAD) and related methods in carbohydrate chemistry

Michael P. Mannino, Alexei Demchenko

University of Missouri-St. Louis

Research output: Chapter in Book/Report/Conference proceeding › Chapter

Abstract

The stereocontrol of glycosylation reactions is a constant struggle in the field of synthetic carbohydrate chemistry. The application of the picoloyl (Pico) substituent can offer numerous stereocontrolling avenues. The most popular application is the Hydrogen-bond-mediated Aglycone Delivery (HAD) method that provides excellent selectivity in the glycosylation of a variety of sugar substrates. The HAD method relies on the formation of an intermolecular hydrogen bond between the nitrogen atom of the Pico substituent on the glycosyl donor with the hydroxy group of the glycosyl acceptor. This interaction provides a facial preference for the nucleophilic attack and hence provides powerful stereocontrol for the glycosidic bond formation. Surveyed herein is the application of the Pico group to stereoselective synthesis of carbohydrates.

Original language	American English
Title of host publication	Carbohydrate Chemistry: Chemical and Biological Approaches Volume 44
DOIs	https://doi.org/10.1039/9781788013864-00093
State	Published - 2020

Disciplines

Biochemistry, Biophysics, and Structural Biology

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Cite this

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abstract = " The stereocontrol of glycosylation reactions is a constant struggle in the field of synthetic carbohydrate chemistry. The application of the picoloyl (Pico) substituent can offer numerous stereocontrolling avenues. The most popular application is the Hydrogen-bond-mediated Aglycone Delivery (HAD) method that provides excellent selectivity in the glycosylation of a variety of sugar substrates. The HAD method relies on the formation of an intermolecular hydrogen bond between the nitrogen atom of the Pico substituent on the glycosyl donor with the hydroxy group of the glycosyl acceptor. This interaction provides a facial preference for the nucleophilic attack and hence provides powerful stereocontrol for the glycosidic bond formation. Surveyed herein is the application of the Pico group to stereoselective synthesis of carbohydrates. ",

author = "Mannino, {Michael P.} and Alexei Demchenko",

note = "The stereocontrol of glycosylation reactions is a constant struggle in the field of synthetic carbohydrate chemistry. The application of the picoloyl (Pico) substituent can offer numerous stereocontrolling avenues. The most popular application is the Hydrogen-bond-mediated Aglycone Delivery (HAD) method that provides excellent selectivity in the glycosylation of a variety of sugar substrates.",

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T1 - Hydrogen-bond-mediated aglycone delivery (HAD) and related methods in carbohydrate chemistry

AU - Mannino, Michael P.

AU - Demchenko, Alexei

N1 - The stereocontrol of glycosylation reactions is a constant struggle in the field of synthetic carbohydrate chemistry. The application of the picoloyl (Pico) substituent can offer numerous stereocontrolling avenues. The most popular application is the Hydrogen-bond-mediated Aglycone Delivery (HAD) method that provides excellent selectivity in the glycosylation of a variety of sugar substrates.

PY - 2020

Y1 - 2020

N2 - The stereocontrol of glycosylation reactions is a constant struggle in the field of synthetic carbohydrate chemistry. The application of the picoloyl (Pico) substituent can offer numerous stereocontrolling avenues. The most popular application is the Hydrogen-bond-mediated Aglycone Delivery (HAD) method that provides excellent selectivity in the glycosylation of a variety of sugar substrates. The HAD method relies on the formation of an intermolecular hydrogen bond between the nitrogen atom of the Pico substituent on the glycosyl donor with the hydroxy group of the glycosyl acceptor. This interaction provides a facial preference for the nucleophilic attack and hence provides powerful stereocontrol for the glycosidic bond formation. Surveyed herein is the application of the Pico group to stereoselective synthesis of carbohydrates.

AB - The stereocontrol of glycosylation reactions is a constant struggle in the field of synthetic carbohydrate chemistry. The application of the picoloyl (Pico) substituent can offer numerous stereocontrolling avenues. The most popular application is the Hydrogen-bond-mediated Aglycone Delivery (HAD) method that provides excellent selectivity in the glycosylation of a variety of sugar substrates. The HAD method relies on the formation of an intermolecular hydrogen bond between the nitrogen atom of the Pico substituent on the glycosyl donor with the hydroxy group of the glycosyl acceptor. This interaction provides a facial preference for the nucleophilic attack and hence provides powerful stereocontrol for the glycosidic bond formation. Surveyed herein is the application of the Pico group to stereoselective synthesis of carbohydrates.

UR - https://pubs.rsc.org/en/content/chapter/bk9781788013680-00093/978-1-78801-368-0

U2 - 10.1039/9781788013864-00093

DO - 10.1039/9781788013864-00093

M3 - Chapter

BT - Carbohydrate Chemistry: Chemical and Biological Approaches Volume 44

ER -

Hydrogen-bond-mediated aglycone delivery (HAD) and related methods in carbohydrate chemistry

Abstract

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