Synthesis of monophosphorylated lipid A precursors using 2-naphthylmethyl ether as a protecting group
نویسندگان
چکیده
منابع مشابه
New insight on 2-naphthylmethyl (NAP) ether as a protecting group in carbohydrate synthesis: a divergent approach towards a high-mannose type oligosaccharide library.
A new method for selective cleavage of 2-naphthylmethyl (NAP) ether utilizing 10-20 molar excess of HF/pyridine in toluene was revealed and strategically applied to a divergent approach towards generation of a high-mannose type oligosaccharide library.
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The use of a combination of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-pinene permits the removal of 2-naphthylmethyl (Nap) ether protecting groups on highly sensitive substrates. The reaction tolerates both acid and base sensitive protecting groups, and products are afforded in 68-96% yield. The utility of the method is demonstrated by the removal of the Nap protecting groups on hig...
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A short and efficient synthesis of 2'-O-methoxyethylguanosine (8) is described. Central to this strategy is the development of a novel silicon-based protecting group (MDPSCl(2), 2) used to protect the 3',5'-hydroxyl groups of the ribose. Silylation of guanosine with 2 proceeded with excellent regioselectivity and in 79% yield. Alkylation of the 2'-hydroxyl group of 6 proceeded with methoxyethyl...
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A number of 5'-O-(4,4'-dimethoxytrityl)thymidine N,N-diisopropylamino phosphoramidites protected at P(III) with derivatives of 2-benzamidoethanol were synthesized and incorporated into synthetic oligonucleotides. Depending on substitution patterns at the alkyl chain, amido group, and phenyl ring, the time required for removal of these protecting groups using concentrated ammonium hydroxide vari...
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ژورنال
عنوان ژورنال: Beilstein Journal of Organic Chemistry
سال: 2020
ISSN: 1860-5397
DOI: 10.3762/bjoc.16.162