Synthesis of (2S,3R,4S),(2S,3S,4R)-epoxyprolines and aminohydroxyprolines

Synthesis of (2S,3R,4S),(2S,3S,4R)-epoxyprolines and aminohydroxyprolines

25, 3R, 4S- and 25, 38, 4R-epoxy-L-prolines were synthesised from trans- 4-hydroxy-L-proline. Assignment of the stereochemical configurations of the epoxy prolines was achieved by n.O.e. studies and chemical correlation. The synthetic utility of the protected epoxides was investigated briefly by rin...

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Bibliografiska uppgifter
Huvudupphovsmän:	Robinson, J, Lee, V, Claridge, T, Baldwin, J, Schofield, C
Materialtyp:	Journal article
Språk:	English
Publicerad:	1998

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av: Baldwin, J, et al.
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THE SYNTHESIS OF POLYHYDROXYLATED AMINO-ACIDS FROM GLUCURONOLACTONE - ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID AND 2R,3R,4R-DIHYDROXYPROLINE
av: Bashyal, B, et al.
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(2R,3R,4R)-Methyl 2-bromo-3,4-dihydroxy-3,4-O-isopropylidenetetrahydrofuran-2-carboxylate
av: Probert, MR, et al.
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SYNTHESIS OF 2R,3S,4R-DIHYDROXYPROLINE FROM D-RIBONOLACTONE
av: Dho, J, et al.
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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
av: Punzo, F, et al.
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2S,3R,4R,5S)-3,4,5-trihydroxypipecolic acid dihydrate [(2S,3R,4R,5S)-3,4,5-tri-hydroxypiperidine-2-carboxylic acid dihydrate]
av: Booth, K, et al.
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(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].
av: Best, D, et al.
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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
av: Simone, M, et al.
Publicerad: (2012)

A PRACTICAL SYNTHESIS OF DEOXYMANNOJIRIMYCIN AND OF (2S, 3R, 4R, 5R)-3,4,5-TRIHYDROXYPIPECOLIC ACID FROM D-GLUCOSE
av: Fleet, G, et al.
Publicerad: (1989)

SYNTHESIS OF (2R,3S,4R)-3,4-DIHYDROXYPROLINE FROM D-RIBONOLACTONE - AN APPROACH TO THE SYNTHESIS OF POLYFUNCTIONALIZED D-AMINO ACIDS FROM SUGAR LACTONES - X-RAY MOLECULAR-STRUCTURES OF 2-AZIDO-3,4-O-(R)-BENZYLIDENE-2-DEOXY-D-RIBONO-1,5-LACTONE, 2-AZIDO-2-DEOXY-D-RIBONO-1,4-LACTONE, AND (2R,3S,3R)-3,4-DIHYDROXYPROLINET
av: Baird, P, et al.
Publicerad: (1987)

ENANTIOSPECIFIC SYNTHESES OF 2S,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2R,3R,4R,5S-TRIHYDROXYPIPECOLIC ACID, 2S,4S,5S-DIHYDROXYPIPECOLIC ACID, AND BULGECININE FROM DEUTERIUM-GLUCURONOLACTONE
av: Bashyal, B, et al.
Publicerad: (1986)

Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4- aminopiperidin-2-ones: Application to the asymmetric synthesis of (+)-(3S,4R)-cisapride
av: Davies, S, et al.
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Asymmetric syntheses of 3,4-syn- and 3,4-anti-3-substituted-4-aminopiperidin-2-ones: application to the asymmetric synthesis of (+)-(3S,4R)-cisapride
av: Davies, S, et al.
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(2R, 3S, 4S, 5R)-Methyl 5-cyano-2,3 : 4,5-di-O-isopropylidene-2,3,4,5-tetrahydroxypentanoate
av: Glawar, A, et al.
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The magnetic states of R(3+) in R(2)NiO(4) (R=Pr, Nd)
av: Boothroyd, A, et al.
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Crystal structure of [(2R,3R,4S)-3,4-bis(acetyloxy)-5-iodo-3,4-dihydro-2H-pyran-2-yl]methyl acetate
av: Zukerman-Schpector, J., et al.
Publicerad: (2015)

Absolute configuration assignment by asymmetric syntheses of the homalium alkaloids (-)-(R,R,R)-hoprominol and (-)-(4'S,4″R,2‴R)-hopromalinol.
av: Davies, S, et al.
Publicerad: (2012)

The asymmetric synthesis of (2R,3R)- and (2R,3S)-3-methyl-aspartates via an enantiodiscrimination strategy
av: Bull, S, et al.
Publicerad: (2001)

Studies on the transformation of nitrosugars into branched chain iminosugars. Part II: Synthesis of (3R,4R,5R,6S)-2,2-bis(hydroxymethyl)azepane-3,4,5,6-tetraol
av: Otero, J, et al.
Publicerad: (2008)

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]
av: Fleet, G, et al.
Publicerad: (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]
av: Fleet, G, et al.
Publicerad: (1990)

ASYMMETRIC-SYNTHESIS OF THE N-TERMINAL COMPONENT OF MICROGININ - (2S,3R)-3-AMINO-2-HYDROXYDECANOIC ACID, ITS (2R,3R)-EPIMER AND (3R)-3-AMINODECANOIC ACID
av: Bunnage, M, et al.
Publicerad: (1995)

ISOLATION FROM CASTANOSPERMUM-AUSTRALE AND X-RAY CRYSTAL-STRUCTURE OF 3,8-DIEPIALEXINE, (1R,2R,3S,7S,8R)-3-HYDROXYMETHYL-1,2,7-TRIHYDROXYPYRROLIZIDINE [(2S,3R,4R,5S,6R)-2-HYDROXYMETHYL-1-AZABICYCLO[3.3.0]OCTAN-3,4,6-TRIOL]
av: Nash, R, et al.
Publicerad: (1988)

Organocatalytic asymmetric total synthesis of (R)-rolipram and formal synthesis of (3S,4R)-paroxetine.
av: Hynes, P, et al.
Publicerad: (2008)

ISOLATION FROM ALEXA-LEIOPETALA AND X-RAY CRYSTAL-STRUCTURE OF ALEXINE, (1R,2R,3R,7S,8S)-3-HYDROXYMETHYL-1,2,7-TRIHYDROXYPYRROLIZIDINE [(2R,3R,4R,5S,6S)-2-HYDROXYMETHYL-1-AZABICYCLO[3.3.0]OCTAN-3,4,6-TRIOL], A UNIQUE PYRROLIZIDINE ALKALOID
av: Nash, R, et al.
Publicerad: (1988)

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.
av: Simone, M, et al.
Publicerad: (2010)

TETRAHYDROISOQUINOLINES .4. ENANTIOSELECTIVE CONVERSION OF (+)-AMPHETAMINE INTO (+)-(1R,3S,4S)-1,2,3,4-TETRAMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE AND (-)-(1S,3S,4R)-1,2,3,4-TETRAMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE VIA TRICARBONYL(ARENE)CHROMIUM METHODOLOGY
av: Coote, S, et al.
Publicerad: (1988)

(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.
av: Jenkinson, S, et al.
Publicerad: (2007)

(3R,4R,5S)-5-(acetamidomethyl)-N-benzyl-3,4-dihydroxytetrahydrofuran-3-carboxamide
av: Punzo, F, et al.
Publicerad: (2005)

ENANTIOSPECIFIC SYNTHESES OF DEOXYMANNOJIRIMYCIN, FAGOMINE AND 2R,5R-DIHYDROXYMETHYL-3R,4R-DIHYDROXYPYRROLIDINE FROM D-GLUCOSE
av: Fleet, G, et al.
Publicerad: (1985)

Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2r,5r-dihydroxymethyl-3r,4r-dihydroxypyrrolidine from D-glucose
av: Fleet, G, et al.
Publicerad: (1985)

Asymmetric synthesis of (4R,5R)-cytoxazone and (4R,5S)-epi-cytoxazone.
av: Davies, S, et al.
Publicerad: (2004)

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

Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (+/-)-3-methylcyclopentene-1-carboxylate.
av: Bunnage, M, et al.
Publicerad: (2003)

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]
av: Edgeley, D, et al.
Publicerad: (2012)

Asymmetric syntheses of (-)-3-epi-Fagomine, (2R,3S,4R)-dihydroxypipecolic acid, and several polyhydroxylated homopipecolic acids.
av: Csatayová, K, et al.
Publicerad: (2014)

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

Stereoselective functionalisation of cis- and trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones: asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids and (2R,3S)-2-amino-2-methyl-3-hydroxy-3-phenylpropanoic acid.
av: Alonso, F, et al.
Publicerad: (2009)

2-Ruled Calibrated 4-folds in R^7 and R^8
av: Lotay, J
Publicerad: (2004)

2-azido-(R)-3,5-O-benzylidene-2-deoxy-2-C-methyl-D-xylono-1,4-lactone [(2S, 4aR, 7R,7aR)-7-azido-7-methyl-2-phenyldihydro-4H-furo[3,2-d][1,3]dioxin6(4aH)-one]
av: Hotchkiss, D, et al.
Publicerad: (2007)