(3R,4R,5S)-5-(acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide

(3R,4R,5S)-5-(acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide

The title compound, C15H20N2O 5, is the first example of a branched tetrahydrofuran sugar amino acid dipeptide isostere incorporated into a peptidomimetic. The crystal structure contains intermolecular N-H⋯O and O-H⋯O hydrogen bonds. © 2005 International Union of Crystallography Printed in Great Bri...

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Bibliografiske detaljer
Main Authors:	Punzo, F, Watkin, D, Simone, M, Fleet, G
Format:	Journal article
Sprog:	English
Udgivet:	2005

Lignende værker

(3R,4R,5R)-5-(Acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide
af: Michela I. Simone, et al.
Udgivet: (2010-11-01)

(3R,4R,5R)-5-(Acetamido-meth-yl)-N-benzyl-3,4-dihy-droxy-tetra-hydro-furan-3-carboxamide.
af: Simone, M, et al.
Udgivet: (2010)

2,5-Anhydro-N-benzyl-2-C-methyl-D-arabinonamide [(2S,3R,4R)-N-benzyl-3,4-dihydroxy-2-methyltetrahydrofuran-2-carboxamide]
af: Cox, D, et al.
Udgivet: (2007)

Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydro-furan-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate
af: Punzo, F, et al.
Udgivet: (2006)

Penta-fluoro-phenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azido-methyl-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxamido]-meth-yl}-3,4-dimeth-oxy-2,3,4,5-tetra-hydro-furan-3-carboxyl-ate.
af: Simone, M, et al.
Udgivet: (2010)

(2S,3R,4R,5R)-3,4-Dihydr-oxy-5-(hydroxy-meth-yl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydr-oxy-5-(hydroxy-meth-yl)proline].
af: Best, D, et al.
Udgivet: (2009)

(2R,3R,4R)-Methyl 2-bromo-3,4-dihydroxy-3,4-O-isopropylidenetetrahydrofuran-2-carboxylate
af: Probert, MR, et al.
Udgivet: (2005)

(2R, 3S, 4S, 5R)-Methyl 5-cyano-2,3 : 4,5-di-O-isopropylidene-2,3,4,5-tetrahydroxypentanoate
af: Glawar, A, et al.
Udgivet: (2005)

3,4-O-isopropylidene-2-C-methl-D-arabinono-1,5-lactone
af: Punzo, F, et al.
Udgivet: (2005)

2S,3R,4R,5S)-3,4,5-trihydroxypipecolic acid dihydrate [(2S,3R,4R,5S)-3,4,5-tri-hydroxypiperidine-2-carboxylic acid dihydrate]
af: Booth, K, et al.
Udgivet: (2007)

(1R,5S,8R)-1,8-dihydroxy-6-oxa-3-azabicyclo[3.2.1]octan-2-one
af: Punzo, F, et al.
Udgivet: (2004)

Synthesis, in silico and in vitro antimicrobial activity of N-(benzyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamides
af: Sergiy V. Vlasov, et al.
Udgivet: (2024-01-01)

Synthesis of three branched iminosugars [(3R,4R,5S)-3-(hydroxymethyl)piperidine-3,4,5-triol, (3R,4R,5R)-3-(hydroxymethyl)piperidine-3,4,5-triol and (3S,4R,5R)-3-(hydroxymethyl)piperidine-3.4,5-triol] and a branched trihydroxynipecotic acid [(3R,4R,5R)-3,4,5-trihydroxypiperidine-3-carboxylic acid] from sugar lactones with a carbon substituent at C-2
af: Simone, M, et al.
Udgivet: (2012)

2-C-azidomethyl-2-deoxy-3,4-O-isopropylidene-D-ribono-1,5-lactone
af: Punzo, F, et al.
Udgivet: (2006)

2-O-Benzhydryl-3,4-(S)-O-benzyl-idene-d-lyxono-1,4-lactone.
af: Jenkinson, S, et al.
Udgivet: (2008)

2-O-Benzhydryl-3,4-(S)-O-benzyl-idene-d-lyxono-1,4-lactone
af: Jenkinson, S, et al.
Udgivet: (2008)

2-O-Benzhydryl-3,4-(S)-O-benzyl-idene-d-xylono-1,4-lactone.
af: Jenkinson, S, et al.
Udgivet: (2008)

(2S,3R,4R,5S)-3,4-O-isopropylidene-2-methyl-1-oxa-6,9-diazaspiro[4.5]decane-7,10-dione
af: Watkins, D, et al.
Udgivet: (2004)

(S)-N-Benzyl-2-methyl-1,2,3,4-tetrahydroisoquinoline-3-carboxamide
af: Glenn. E.M. Maguire, et al.
Udgivet: (2011-01-01)

1-deoxy-4-C-hydroxymethyl-3,4-O-isopropylidene-beta-L-ribulofuranose [(2R,3S,4S)-4-(hydroxymethyl)-3,4-O-isopropylidene-2-methyltetrahydrofuran-2,3,4-triol]
af: Best, D, et al.
Udgivet: (2007)

3,4 : 5,6-di-O-isopropylidene-3-C-hydroxy-methyl-D-altrono-1,3 '-lactone
af: Parker, S, et al.
Udgivet: (2006)

1-Benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate
af: Caracelli, I., et al.
Udgivet: (2010)

N-(2-Carboxyethyl)-2,5-dideoxy-2,5-imino-D-mannonic acid [(3R,4R,5R)-1-(2-carboxyethyl)-3,4-dihydroxy-5-hydroxymethyl-L-proline]
af: Edgeley, D, et al.
Udgivet: (2012)

2,3-O-isopropylidene-L-apiono-1,4-lactone [(3S, 4S)-3,4-dihydroxy-4-(hydroxymethyl)-3,4-di-O-isopropylidene-4,5-dihydrofuran-2(3H)-one]
af: Best, D, et al.
Udgivet: (2007)

1-Benzyl-2,5-dioxopyrrolidine-3,4-diyl diacetate
af: Edward R. T. Tiekink, et al.
Udgivet: (2010-12-01)

SYNTHESIS OF HOMOCHIRAL BETA-HYDROXY-ALPHA-AMINO-ACIDS [(2S,3R,4R)-3,4-DIHYDROXYPROLINE AND (2S,3R,4R)-3,4-DIHYDROXYPIPECOLIC ACID] AND OF 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL [DAB1] AND FAGOMINE [1,5-IMINO-1,2,5-TRIDEOXY-D-ARABINO-HEXITOL]
af: Fleet, G, et al.
Udgivet: (1990)

Synthesis of homochiral β-hydroxy-α-aminoacids [(2S,3R,4R)-3,4-dihydroxyproline and (2S,3R,4R)-3,4-dihydroxypipecolic aicd] and of 1,4-dideoxy-1,4-imino-D-arabinitol [DAB1] and fagomine [1,5-imino-1,2,5-trideoxy-D-arabino-hexitol]
af: Fleet, G, et al.
Udgivet: (1990)

2-azido-2-deoxy-3,4-O-isopropylidene-2-C-methyl-D-ribono-1,5-lactone
af: Punzo, F, et al.
Udgivet: (2005)

(4S,5R,6R)-Methyl 4-hydr-oxy-4,5-iso-propyl-idenedioxy-4,5,6,7-tetra-hydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxyl-ate.
af: Jenkinson, S, et al.
Udgivet: (2009)

(2R,5S)-2-Trichloromethyl-3-oxa-1-azabicyclo-[3.3.0]octane-4,8-dione
af: Punzo, F, et al.
Udgivet: (2005)

Synthesis and antitumor properties of some new N-(5-R-benzyl-1,3-thiazol-2-yl)-4,5-dihydro-1H-imidazole-2-carboxamides
af: Volodymyr Ya Horishny, et al.
Udgivet: (2020-08-01)

2,4-Dimethyl-3,4-O-isopropylidene-L-arabinono-1,5-lactone
af: Booth, K, et al.
Udgivet: (2007)

N-(2-Carboxyethyl)-2,5-dideoxy-2,5-imino-d-mannonic acid [(3R,4R,5R)-1-(2-carboxyethyl)-3,4-dihydroxy-5-hydroxymethyl-l-proline]
af: David S. Edgeley, et al.
Udgivet: (2012-10-01)

Erratum: (4S,5R,6R)-Methyl 4-hydr-oxy-4,5-iso-propyl-idenedioxy-4,5,6,7-tetra-hydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxyl-ate. Erratum.
af: Jenkinson, S, et al.
Udgivet: (2009)

(4S,5R,6R)-Methyl 4-hydroxy-4,5-isopropylidenedioxy-4,5,6,7-tetrahydro-1,2,3-triazolo[1,5-a]pyridine-3-carboxylate. Erratum
af: Sarah F. Jenkinson, et al.
Udgivet: (2009-09-01)

(S)-3-Dimethyl-amino-2-{(4S,5R)-5-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hydroxy-propanoic acid.
af: Jenkinson, S, et al.
Udgivet: (2007)

Crystal structure of (3S,4R,5R)-5-bromomethyl-3,4-isopropylidenedioxy- 3,4-dihydro-5/2-pyrrole-l-oxide, C8H12BrNO3
af: Frey W., et al.
Udgivet: (2003-12-01)

Crystal structure of (3S,4R,5R)-5-bromomethyl-3,4-isopropylidenedioxy- 3,4-dihydro-5H-pyrrole-1-oxide, C8H12BrNO3
af: Frey W., et al.
Udgivet: (2003-03-01)

2,3-C-Dimethyl-3,4-O-isopropylidene-D-allono-1,5-lactone
af: Curran, L, et al.
Udgivet: (2007)

Study on the regioselectivity of the N-ethylation reaction of N-benzyl-4-oxo-1,4-dihydroquinoline-3-carboxamide
af: Pedro N. Batalha, et al.
Udgivet: (2019-02-01)