The Synthesis of Allosamidin and Its Analogue Di-N-Acetyl-β-Chitobiosyl NAG-Thiazoline Using the Photosensitive o-Nitrobenzyl Ether Tether as Linker

Author(s): Gangliang Huang, Fei Cheng.

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 8 , 2012

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Abstract:

The solid-phase synthesis of allosamidin and its analogue di-N-acetyl-β-chitobiosyl NAG-thiazoline were investigated. The synthesis was performed using polystyrene as support and o-nitrobenzyl ether tether as linker. The target allosamidin 1 and di-N-acetyl-β-chitobiosyl N-acetylglucosamine (NAG)-thiazoline 2 were efficiently obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, deacetylation, and photolysis, respectively.

Keywords: Allosamidin and its analogue, glycosylation reactions, o-nitrobenzyl ether, solid-phase synthesis, N-acetylglucosamine, filtration, byproducts, organic synthesis, oxygen, chloride.

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Article Details

VOLUME: 9
ISSUE: 8
Year: 2012
Page: [577 - 579]
Pages: 3
DOI: 10.2174/157017812802850267

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