Concerning the Synthesis of D-Mannosamine and D-Glucosamine from D-arabo-3,4,5,6-Tetraacetoxy-1-nitro-1-hexene

Sowden, John C.; Oftedahl, Marvin L.

doi:10.1021/ja01494a050

Cited by 31 publications

(3 citation statements)

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“…(46), mint kiindulási anyagot állítjuk elő, amelyre van példa az irodalomban. [66][67][68] Ezek közül az egyik leggyakrabban alkalmazott módszer a D-arabinózból (47) kiinduló 5 lépéses szintézis (10. ábra). 66 Első lépése a D-arabinóz (47) nitrometános lánchosszabbítása, amely a megfelelő 1-dezoxi-1-nitro-D-glücitolt (48) és 1-dezoxi-1-nitro-D-mannitolt (49) eredményezi.…”

Section: A 2-amino-2-dezoxi-d-glükopiranozil-karbonsav: H-glcapc-ohunclassified

“…[66][67][68] Ezek közül az egyik leggyakrabban alkalmazott módszer a D-arabinózból (47) kiinduló 5 lépéses szintézis (10. ábra). 66 Első lépése a D-arabinóz (47) nitrometános lánchosszabbítása, amely a megfelelő 1-dezoxi-1-nitro-D-glücitolt (48) és 1-dezoxi-1-nitro-D-mannitolt (49) eredményezi. Ezt a keveréket acetilezve és lúgosan hidrolizálva kapható a kulcsintermedier 1,2-telítetlen vegyület (50).…”

Section: A 2-amino-2-dezoxi-d-glükopiranozil-karbonsav: H-glcapc-ohunclassified

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Új β-cukoraminosavak előállítása és beépítése foldamerekbe

Gőz¹

2019

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Section: A 2-amino-2-dezoxi-d-glükopiranozil-karbonsav: H-glcapc-ohunclassified

Új β-cukoraminosavak előállítása és beépítése foldamerekbe

Gőz¹

2019

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“…Mannosamine can also be obtained by alkaline epimerization of 2‐hydroxyl group of a glucosamine derivative . A classical strategy for the synthesis of mannosamine is to replace 2‐hydroxyl group of mannitol derivatives with an amino group followed by selective oxidation to obtain an aldose . Chemical approaches to prepare 2‐aminohexose include introduction of an azido function followed by reduction of the azido group into amine.…”

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Convenient Synthesis of Glucosamine and Mannosamine Starting from Glucose

Kim

Cho

2015

Bulletin Korean Chem Soc

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TheNef Reaction

Pinnick

1990

Organic Reactions

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The Nef reaction is usually defined as the conversion of a primary or secondary nitroalkane into the corresponding carbonyl compound. This reaction was reported by the Swiss chemist J. U. Nef in 1894. Hydrochloric and sulfuric acid give the same result. The conversion of a nitro group to a carbonyl group has become an important synthetic tool because of the ease of preparation of substituted nitro compounds by condensation of nitroalkanes with aldehydes (the Henry reaction), conjugate addition of nitroalkanes to electrophilic alkenes, or carbon alkylation of the dianion of primary nitroparaffins. The Nef reaction is one of the better examples of “umpolung” reactivity in which the original nitro compound anion functions as an acyl anion equivalent. This chapter discusses the Nef reaction and modifications of the original process that extend the variety of compounds which are useful as substrates. Each modification is considered according to general mechanistic type and is organized in a “reagent” approach. The Tabular Survey lists all known examples of both the Nef reaction and these modifications so that specific comparison of methods can be made.

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Concerning the Synthesis of D-Mannosamine and D-Glucosamine from D-arabo-3,4,5,6-Tetraacetoxy-1-nitro-1-hexene

Cited by 31 publications

References 0 publications

Új β-cukoraminosavak előállítása és beépítése foldamerekbe

Új β-cukoraminosavak előállítása és beépítése foldamerekbe

Convenient Synthesis of Glucosamine and Mannosamine Starting from Glucose

TheNef Reaction

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