(1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate

(1<i>R</i>,2<i>R</i>,3<i>S</i>,4<i>R</i>)-1-(Acetylamino)-2,4,5-tris(acetyloxy)-1-((2<i>S</i>)-4-(benzyloxy)-5-oxo-2,5-dihydrofuran-2-yl)pentan-3-yl Acetate

Treatment of <i>N</i>-acetylneuraminic acid with excess base in the presence of benzyl bromide gives a polyhydroxylated 1,4 lactone which after acetylation gave the title compound in 20% overall yield. The structure of the product was confirmed by single crystal X-ray diffraction analysi...

Full description

Bibliographic Details
Main Authors:	Liam S. Fitzgerald, Ciaran O’Malley, Paul V. Murphy
Format:	Article
Language:	English
Published:	MDPI AG 2022-02-01
Series:	Molbank
Subjects:	sialic acid N-acetylneuraminic acid 1,4 lactones γ-lactones polyhydroxylated compounds
Online Access:	https://www.mdpi.com/1422-8599/2022/1/M1337

Similar Items

4-Phenylnaphtho[2,3-<i>c</i>]furan-1(3<i>H</i>)-one, 9-Phenylnaphtho[2,3-<i>c</i>]furan-1(3<i>H</i>)-one and 3<i>a</i>,4-Dihydro-9-phenylnaphtho[2,3-<i>c</i>]furan-1(3<i>H</i>)-one Crystal Structures
by: Nabyl Merbouh, et al.
Published: (2021-07-01)

(2<i>R</i>, 4<i>S</i>, 5<i>S</i>) 1-(4-(4-(((7-Chloroquinolin-4-yl)amino)methyl)-1<i>H</i>-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1<i>H</i>,3<i>H</i>)-dione
by: Houin Kuan, et al.
Published: (2023-07-01)

δ-Lactones—A New Class of Compounds That Are Toxic to <i>E. coli</i> K12 and R2–R4 Strains
by: Paweł Kowalczyk, et al.
Published: (2021-05-01)

6-[(2<i>S</i>,3<i>R</i>)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1<i>H</i>-1,2,4-triazol-1-yl)butan-2-yl]-5-fluoropyrimidine-4-carbaldehyde
by: Joana L. C. Sousa, et al.
Published: (2023-03-01)

(1<i>R</i>,2<i>S</i>,5<i>R</i>)-2-Isopropyl-5-methylcyclohexyl (<i>R</i>)-4-methylbenzenesulfonimidate
by: Arianna Tota, et al.
Published: (2022-12-01)

tert-Butyl (2S,3R,4R)-7′-bromo-4-methyl-2′,5-dioxo-4,5-dihydro-3H-spiro[furan-2,3′-indoline]-3-carboxylate
by: Chen-Hong Meng, et al.
Published: (2017-03-01)

(<i>R</i>,<i>S</i>)-2-{[4-(4-Methoxyphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl] thio}-1-phenyl-1-ethanol
by: Flavius-Gabriel Wurfer, et al.
Published: (2021-06-01)

(<i>R</i>,<i>S</i>)-2-{[4-(4-Methylphenyl)-5-phenyl-4<i>H</i>-1,2,4-triazol-3-yl]thio}-1-phenyl-1-ethanol
by: Vladislav-Silvestru Valicsek, et al.
Published: (2021-07-01)

A Novel PCC-Catalyzed Process Involving the Oxidative Cleavage of an α-Bromomethyl-tetrahydrofuran Bond. Synthesis of (2S,3R)-2-{(R)-Bromo[(2R,3R,5S,6R)-3,5-dibromo-6-ethyltetrahydro-2H-pyran-2-yl]methyl}-5-oxotetrahydrofuran-3-yl Benzoate
by: Vincenzo Piccialli
Published: (2017-12-01)

(2<i>S</i>,2’<i>S</i>,4<i>R</i>,5<i>S</i>,5’<i>R</i>)-2,2’-Di-<i>tert</i>-butyl-4-hydroxy-5,5’-dimethyl-4,5’-bi(1,3-dioxolanyl)-4’-one
by: R. Alan Aitken, et al.
Published: (2023-07-01)

(1<i>R</i>,2<i>R</i>,6<i>S</i>)-2(4-(4-Isopropylbenzyl)piperazin-1-yl)-3-methyl-6-(prop-1-en-2-yl)cyclohex-3-enol
by: Alexandra V. Podturkina, et al.
Published: (2023-01-01)

(<i>E</i>)-2-(6-(4′-(Diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazin-5(4<i>H</i>)-ylidene)-2-(6-(4′-(diphenylamino)-[1,1′-biphenyl]-2-yl)-[1,2,5]oxadiazolo[3,4-<i>b</i>]pyrazin-5-yl)acetonitrile
by: Yuriy A. Kvashnin, et al.
Published: (2023-08-01)

(±)-((2<i>S</i>,5<i>R</i>)-5-(Acetoxymethyl)tetrahydrofuran-2-yl)methyl Benzoate
by: Vincenzo Piccialli
Published: (2022-03-01)

Diethyl (5-Benzyl-2-(4-(<i>N</i>′-hydroxycarbamimidoyl)phenyl)-5-methyl-4,5-dihydrofuran-3-yl)phosphonate
by: Oscar Leonardo Avendaño Leon, et al.
Published: (2023-10-01)

(1<i>R</i>,2<i>R</i>,4<i>R</i>)-<i>N</i>-((4-((4-(2-Carboxyethyl)phenoxy)methyl)thiophen-2-yl)methyl)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-aminium Chloride
by: Sergey O. Kuranov, et al.
Published: (2023-04-01)

Synthesis and Characterization of Novel 2-(1,2,3-Triazol-4-yl)-4,5-dihydro-1<i>H</i>-pyrazol-1-yl)thiazoles and 2-(4,5-Dihydro-1<i>H</i>-pyrazol-1-yl)-4-(1<i>H</i>-1,2,3-triazol-4-yl)thiazoles
by: Benson M. Kariuki, et al.
Published: (2022-12-01)

Metal-Catalyzed Synthesis and Transformations of <i>β</i>-Haloenol Esters
by: Victorio Cadierno
Published: (2020-04-01)

1,4-Bis(2-((1<i>R</i>,5<i>S</i>)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethyl)piperazine
by: Nikolai S. Li-Zhulanov, et al.
Published: (2024-02-01)

(2<i>Z</i>,5<i>Z</i>)-5-((3-(Benzofuran-2-yl)-1-phenyl-1<i>H</i>-pyrazol-4-yl)methylene)-2-((4-methoxyphenyl)imino)-3-phenylthiazolidin-4-one
by: Bakr F. Abdel-Wahab, et al.
Published: (2023-06-01)

Fosbergenone: 3-[2-(1,2,5,5-Tetramethyl-7-oxo-1,2,3,4,4<i>a</i>,5,6,7-octahydronaphthalen-1-yl)ethyl]-2,5-dihydrofuran-2-one
by: Joy Ebenezer Rajakulendran, et al.
Published: (2022-06-01)

(1<i>S</i>,5<i>R</i>)-6,6-Dimethyl-4-(((1<i>S</i>,2<i>S</i>,5<i>S</i>)-2,6,6-trimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)methyl)bicyclo[3.1.1]hept-3-en-2-one
by: Oleg V. Ardashov, et al.
Published: (2022-10-01)

Synthesis and Characterization of Some New Metal Complexes of (5-C-Dimethyl Malonyl-Pentulose-Î³Lactone-2,3-Enedibenzoate)
by: A-J. A. Mukhlis, et al.
Published: (2017-05-01)

1-{(1<i>S</i>,2<i>S</i>,4<i>R</i>)-7,7-Dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo [2.2.1]heptan-2-yl}-1<i>H</i>-benzo[<i>d</i>]imidazole
by: Luka Ciber, et al.
Published: (2023-01-01)

<i>N</i><sup>1</sup>-{4-[2-(Methylthio)-1<i>H</i>-imidazol-5-yl]pyridin-2-yl}benzene-1,4-diamine
by: Ahmed El-Gokha, et al.
Published: (2019-02-01)

(<i>±</i>)-2-(2-Fluoro-[1,1′-biphenyl]-4-yl)-<i>N</i>-(1-phenylpropan-2-yl)propanamide
by: Stanimir Manolov, et al.
Published: (2022-01-01)

2-(3,5-Dimethyl-1<i>H</i>-pyrazol-1-yl)thiazolo[4,5-<i>b</i>]pyridine
by: Honghong Lan, et al.
Published: (2019-08-01)

Correction: Rajakulendran et al. Fosbergenone: 3-[2-(1,2,5,5-Tetramethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl)ethyl]-2,5-dihydrofuran-2-one. <i>Molbank</i> 2022, <i>2022</i>, M1391
by: Joy Ebenezer Rajakulendran, et al.
Published: (2023-02-01)

(<i>Z</i>)-2′-((Adamantan-1-yl)thio)-1,1′-dimethyl-2′,3′-dihydro-[2,4′-biimidazolylidene]-4,5,5′(1<i>H</i>,1′<i>H</i>,3<i>H</i>)-trione
by: Vladimir Burmistrov, et al.
Published: (2023-02-01)

2-((4-Amino-5-((2,4-dichlorophenoxy)methyl)-4<i>H</i>-1,2,4-triazol-3-yl)thio)-1-(5-methyl-1-(4-nitrophenyl)-1<i>H</i>-1,2,3-triazol-4-yl)ethan-1-one
by: Bakr F. Abdel-Wahab, et al.
Published: (2023-09-01)

<i>rel</i>-2-[4-Chloro-2-[(5<i>R</i>,6<i>R</i>,7<i>S</i>)-6-[5-(4-methoxyphenyl)-3-(2-naphthyl)-3,4-dihydropyrazole-2-carbonyl]-5-methyl-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-<i>d</i>]thiazol-7-yl]phenoxy]acetic Acid
by: Ihor Yushyn, et al.
Published: (2022-07-01)

(<i>E</i>)-1-(5-Methyl-1-(4-nitrophenyl)-1<i>H</i>-1,2,3-triazol-4-yl)-3-(naphthalen-2-yl)prop-2-en-1-one
by: Benson M. Kariuki, et al.
Published: (2022-10-01)

1-Benzyl-2-(thien-2-yl)-4,5-dihydro-1<i>H</i>-imidazole
by: Alexandra S. Golubenkova, et al.
Published: (2020-05-01)

<i>N</i>-Benzo[<i>c</i>][1,2,5]thiazol-4-yl-3-trifluoromethylbenzamide
by: Hamad H. Al Mamari, et al.
Published: (2019-07-01)

2-((5-(5-Methyl-2-phenyl-1<i>H</i>-imidazol-4-yl)-1,3,4-oxadiazol-2-yl)thio)-1-phenylethan-1-one
by: Bakr F. Abdel-Wahab, et al.
Published: (2023-06-01)

Pharyngeal Pumping and Tissue-Specific Transgenic P-Glycoprotein Expression Influence Macrocyclic Lactone Susceptibility in <i>Caenorhabditis elegans</i>
by: Alexander P. Gerhard, et al.
Published: (2021-02-01)

3-(3,4-Dichlorophenyl)-5-(1<i>H</i>-indol-5-yl)-1,2,4-oxadiazole
by: Julia A. Efimova, et al.
Published: (2023-01-01)

2-((4-Phenyl-5-(2-(<i>p</i>-tolylamino)ethyl)-4<i>H</i>-1,2,4-triazol-3-yl)thio)-<i>N</i>′-(1-phenylethylidene)acetohydrazide
by: Aida Šermukšnytė, et al.
Published: (2022-06-01)

Experimental Comparative Study of Dynamic Behavior in Solution Phase of <i>C</i>-Tetra(phenyl)resorcin[4]arene and <i>C</i>-Tetra(phenyl)pyrogallol[4]arene
by: José Luis Casas-Hinestroza, et al.
Published: (2020-05-01)

New Morphiceptin Peptidomimetic Incorporating (1<i>S</i>,2<i>R</i>,3<i>S</i>,4<i>S</i>,5<i>R</i>)-2-Amino-3,4,5-trihydroxycyclopen-tane-1-carboxylic acid: Synthesis and Structural Study
by: Raquel Soengas, et al.
Published: (2020-06-01)

4-(2,5-Dimethyl-1<i>H</i>-pyrrol-1-yl)-1,2,5-oxadiazol-3-amine
by: Natalia V. Obruchnikova, et al.
Published: (2023-07-01)