Formation of β-Configured Thioglycosides of D-Glucosamine and D-Galactosamine and Synthesis of Protected Human Milk Oligosaccharides

Kamilla Pedersen; Louise G. Christensen; Henrik H. Jensen

doi:10.1021/acs.joc.3c01267

Formation of β-Configured Thioglycosides of D-Glucosamine and D-Galactosamine and Synthesis of Protected Human Milk Oligosaccharides

Kamilla Pedersen, Louise G. Christensen, Henrik H. Jensen^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

Abstract

We report on the stereoselective multigram scale preparation of cyclohexyl- and phenyl thioglycosides of 2-azido-2-deoxy-β-d-gluco- and galactopyranosides from d-N-acetylglucosamine using a catalytic and solvent-free method. Two of the prepared building blocks were used as key intermediates for the synthesis of human milk oligosaccharides LNT and LNnT in their protected form.

Original language	English
Journal	Journal of Organic Chemistry
Volume	88
Issue	17
Pages (from-to)	12531–12541
Number of pages	11
ISSN	0022-3263
DOIs	https://doi.org/10.1021/acs.joc.3c01267
Publication status	Published - 1 Sept 2023

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abstract = "We report on the stereoselective multigram scale preparation of cyclohexyl- and phenyl thioglycosides of 2-azido-2-deoxy-β-d-gluco- and galactopyranosides from d-N-acetylglucosamine using a catalytic and solvent-free method. Two of the prepared building blocks were used as key intermediates for the synthesis of human milk oligosaccharides LNT and LNnT in their protected form.",

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Formation of β-Configured Thioglycosides of D-Glucosamine and D-Galactosamine and Synthesis of Protected Human Milk Oligosaccharides. / Pedersen, Kamilla; Christensen, Louise G.; Jensen, Henrik H.
In: Journal of Organic Chemistry, Vol. 88, No. 17, 01.09.2023, p. 12531–12541.

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaper › Journal article › Research › peer-review

TY - JOUR

T1 - Formation of β-Configured Thioglycosides of D-Glucosamine and D-Galactosamine and Synthesis of Protected Human Milk Oligosaccharides

AU - Pedersen, Kamilla

AU - Christensen, Louise G.

AU - Jensen, Henrik H.

PY - 2023/9/1

Y1 - 2023/9/1

N2 - We report on the stereoselective multigram scale preparation of cyclohexyl- and phenyl thioglycosides of 2-azido-2-deoxy-β-d-gluco- and galactopyranosides from d-N-acetylglucosamine using a catalytic and solvent-free method. Two of the prepared building blocks were used as key intermediates for the synthesis of human milk oligosaccharides LNT and LNnT in their protected form.

AB - We report on the stereoselective multigram scale preparation of cyclohexyl- and phenyl thioglycosides of 2-azido-2-deoxy-β-d-gluco- and galactopyranosides from d-N-acetylglucosamine using a catalytic and solvent-free method. Two of the prepared building blocks were used as key intermediates for the synthesis of human milk oligosaccharides LNT and LNnT in their protected form.

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U2 - 10.1021/acs.joc.3c01267

DO - 10.1021/acs.joc.3c01267

M3 - Journal article

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AN - SCOPUS:85169162127

SN - 0022-3263

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SP - 12531

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JF - Journal of Organic Chemistry

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ER -

Formation of β-Configured Thioglycosides of D-Glucosamine and D-Galactosamine and Synthesis of Protected Human Milk Oligosaccharides

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