Synthesis of Allosamidin Analogue Di-N-acetyl-β-chitobiosyl N-Glycoaminooxazoline

Gangliang      Huang; Shuangquan      Shu; Fei      Cheng

Abstract

The solid-phase synthesis of di-N-acetyl-β-chitobiosyl N-glycoaminooxazoline 2 was studied. The synthesis was gone along using the N-benzyloxycarbonyl (Cbz) protected trichloroacetimidates 11 and 13 as donors, polystyrene as support, and o-nitrobenzyl ether tether as linker. The compound 2 was high-efficiently offered by three glycosylations, catalytic hydrogenolysis, acetylation, deacetylation, and photolysis, respectively.

Keywords: Di-N-acetyl-β-chitobiosyl N-glycoaminooxazoline, Solid-phase synthesis, Glycosylation, Analogue.

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Letters in Drug Design & Discovery

Title:Synthesis of Allosamidin Analogue Di-N-acetyl-β-chitobiosyl N-Glycoaminooxazoline

Volume: 10 Issue: 8

Author(s): Gangliang Huang, Shuangquan Shu and Fei Cheng

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Keywords: Di-N-acetyl-β-chitobiosyl N-glycoaminooxazoline, Solid-phase synthesis, Glycosylation, Analogue.

Abstract: The solid-phase synthesis of di-N-acetyl-β-chitobiosyl N-glycoaminooxazoline 2 was studied. The synthesis was gone along using the N-benzyloxycarbonyl (Cbz) protected trichloroacetimidates 11 and 13 as donors, polystyrene as support, and o-nitrobenzyl ether tether as linker. The compound 2 was high-efficiently offered by three glycosylations, catalytic hydrogenolysis, acetylation, deacetylation, and photolysis, respectively.

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Huang Gangliang, Shu Shuangquan and Cheng Fei, Synthesis of Allosamidin Analogue Di-N-acetyl-β-chitobiosyl N-Glycoaminooxazoline, Letters in Drug Design & Discovery 2013; 10 (8) . https://dx.doi.org/10.2174/15701808113109990008