A convenient synthesis of the core trisaccharide of the N-glycans

Zhichao Lu; Ning Ding; Wei Zhang; Peng Wang; Yingxia Li

doi:10.1016/j.tetlet.2011.04.060

A convenient synthesis of the core trisaccharide of the N-glycans

Zhichao Lu, Ning Ding, Wei Zhang, Peng Wang, Yingxia Li

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

6 Scopus citations

Abstract

A convenient synthesis of the core trisaccharide of the N-glycans was described. Orthogonal one-pot glycosylation of three monosaccharide building blocks was performed to furnish β-glucosyl chitobiose, which was then transformed to β-mannosyl chitobiose by intramolecular epimerization of the C-2 position of the β-glucoside. The key glucosyl donor 7c with differentiated 2,3-OH was prepared following the 4,6-O-benzylidene-protected 1,2-orthoester strategy.

Original language	English
Pages (from-to)	3320-3323
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2011.04.060
State	Published - 29 Jun 2011
Externally published	Yes

Keywords

1,2-Orthoester
Core trisaccharide
N-Glycan
One-pot glycosylation

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10.1016/j.tetlet.2011.04.060

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title = "A convenient synthesis of the core trisaccharide of the N-glycans",

abstract = "A convenient synthesis of the core trisaccharide of the N-glycans was described. Orthogonal one-pot glycosylation of three monosaccharide building blocks was performed to furnish β-glucosyl chitobiose, which was then transformed to β-mannosyl chitobiose by intramolecular epimerization of the C-2 position of the β-glucoside. The key glucosyl donor 7c with differentiated 2,3-OH was prepared following the 4,6-O-benzylidene-protected 1,2-orthoester strategy.",

keywords = "1,2-Orthoester, Core trisaccharide, N-Glycan, One-pot glycosylation",

author = "Zhichao Lu and Ning Ding and Wei Zhang and Peng Wang and Yingxia Li",

note = "Funding Information: This work is supported by the National Nature Science Foundation of China (NSFC21002014) and the Fundamental Research Funds for the Central Universities of China.",

year = "2011",

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doi = "10.1016/j.tetlet.2011.04.060",

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T1 - A convenient synthesis of the core trisaccharide of the N-glycans

AU - Lu, Zhichao

AU - Ding, Ning

AU - Zhang, Wei

AU - Wang, Peng

AU - Li, Yingxia

N1 - Funding Information: This work is supported by the National Nature Science Foundation of China (NSFC21002014) and the Fundamental Research Funds for the Central Universities of China.

PY - 2011/6/29

Y1 - 2011/6/29

N2 - A convenient synthesis of the core trisaccharide of the N-glycans was described. Orthogonal one-pot glycosylation of three monosaccharide building blocks was performed to furnish β-glucosyl chitobiose, which was then transformed to β-mannosyl chitobiose by intramolecular epimerization of the C-2 position of the β-glucoside. The key glucosyl donor 7c with differentiated 2,3-OH was prepared following the 4,6-O-benzylidene-protected 1,2-orthoester strategy.

AB - A convenient synthesis of the core trisaccharide of the N-glycans was described. Orthogonal one-pot glycosylation of three monosaccharide building blocks was performed to furnish β-glucosyl chitobiose, which was then transformed to β-mannosyl chitobiose by intramolecular epimerization of the C-2 position of the β-glucoside. The key glucosyl donor 7c with differentiated 2,3-OH was prepared following the 4,6-O-benzylidene-protected 1,2-orthoester strategy.

KW - 1,2-Orthoester

KW - Core trisaccharide

KW - N-Glycan

KW - One-pot glycosylation

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U2 - 10.1016/j.tetlet.2011.04.060

DO - 10.1016/j.tetlet.2011.04.060

M3 - Article

AN - SCOPUS:79957622978

SN - 0040-4039

VL - 52

SP - 3320

EP - 3323

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

A convenient synthesis of the core trisaccharide of the N-glycans

Abstract

Keywords

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