Rapid and Stereoselective Access to 6″-Amino-6″-deoxy-α-GalCer Scaffolds

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Title

Rapid and Stereoselective Access to 6″-Amino-6″-deoxy-α-GalCer Scaffolds

Content partner

University of Otago

Collection

Otago University Research Archive

Description

This work describes a highly efficient route to an orthogonally protected α-galactosylphytosphingosine (α-GalPhyt) from which 6″-N-modified α-galactosylceramide (α-GalCer) analogues can be synthesized rapidly and on-scale. Key to this route is the use of a d-galactal-derived 1,2-anhydro donor that undergoes an α-selective glycosylation with a sphingoid acceptor. The resulting α-GalPhyt intermediate can be orthogonally deprotected, enabling selective manipulation at either the C-6″ position of...

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Format

Research paper

Research format

Scholarly text / Journal article

Thesis level

Article

Date created

2025-03-04

Creator

Winefield, Kaleb C / Larsen, David S / Painter, Gavin F / Compton, Benjamin J

URL

https://hdl.handle.net/10523/45232

Related subjects

α-Galactosylceramide / synthetic glycolipids / NKT cells / natural killer T cells

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