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- W2953196600 abstract "Abstract Novel lipid A analogues which possess four ( R )-3-hydroxyacyl moieties of shorter chain length were synthesized via a new divergent synthetic route in order to clarify the effect of the chain length of acyl groups to the biological activity: a disaccharide 4′-phosphate was first constructed as a common synthetic intermediate and all acyl moieties were then introduced step by step to the respective positions. The hydroxy group in acyl moieties was protected with a benzyl group by novel 1-pot reductive alkylation using benzaldehyde, TMS 2 O, TMSOTf, and Et 3 SiH. Both the glycosyl donor and acceptor were synthesized by using the new method recently reported by ourselves for the regioselective reductive opening of 4,6- O -benzylidene glucosamine derivatives with BH 3 ·Me 2 NH and BF 3 ·OEt 2 . In this reaction, a 3- O -allyloxycarbonylated 4,6- O -benzylidene compound in CH 3 CN afforded the 6- O -benzylated product selectively, which was then converted to a glycosyl trichloroacetimidate used as the donor. The 4- O -benzylated acceptor was synthesized by the same reductive opening of a 3- O -p-methoxybenzylated compound in CH 2 Cl 2 . A disaccharide 4′-phosphate was synthesized by coupling of the imidate donor and the acceptor using TMSOTf as a catalyst. ( R )-3-Benzyloxyacyl groups were then introduced to the 3,3′, 2 and 2′ positions followed by 1- O -phosphorylation and subsequent deprotection by Pd H 2 afforded the desired lipid A analogues. The present divergent route opens an efficient way toward the synthesis of lipid A libraries. Biological tests (inhibition of IL-6 induction) clearly showed the critical importance of the chain length of the acyl moieties in lipid A to the activity." @default.
- W2953196600 created "2019-06-27" @default.
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- W2953196600 date "2010-06-20" @default.
- W2953196600 modified "2023-09-24" @default.
- W2953196600 title "ChemInform Abstract: Divergent Synthesis and Biological Activities of Lipid A Analogues of Shorter Acyl Chains" @default.
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- W2953196600 doi "https://doi.org/10.1002/chin.199830263" @default.
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