A versatile approach to the synthesis of mannosamine glycosides

Catherine Alex; Satsawat Visansirikul; Alexei Demchenko

doi:10.1039/D0OB01640C

A versatile approach to the synthesis of mannosamine glycosides

Catherine Alex, Satsawat Visansirikul, Alexei Demchenko

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

Abstract

O -Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O -picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3- O -benzoyl group.

Original language	American English
Journal	Organic and Biomolecular Chemistry
DOIs	https://doi.org/10.1039/D0OB01640C
State	Published - 2020

Disciplines

Biochemistry, Biophysics, and Structural Biology

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title = "A versatile approach to the synthesis of mannosamine glycosides",

abstract = " O -Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O -picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3- O -benzoyl group. ",

author = "Catherine Alex and Satsawat Visansirikul and Alexei Demchenko",

note = "O-Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl grou",

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doi = "10.1039/D0OB01640C",

language = "American English",

journal = "Organic and Biomolecular Chemistry",

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T1 - A versatile approach to the synthesis of mannosamine glycosides

AU - Alex, Catherine

AU - Visansirikul, Satsawat

AU - Demchenko, Alexei

N1 - O-Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl grou

PY - 2020

Y1 - 2020

N2 - O -Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O -picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3- O -benzoyl group.

AB - O -Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O -picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3- O -benzoyl group.

UR - https://doi.org/10.1039/D0OB01640C

U2 - 10.1039/D0OB01640C

DO - 10.1039/D0OB01640C

M3 - Article

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

A versatile approach to the synthesis of mannosamine glycosides

Abstract

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