Preliminary studies on the transformation of nitrosugars into branched chain iminosugars: synthesis of 1,4-dideoxy-4-C-hydroxymethyl-1,4-imino-pentanols.

Preliminary studies on the transformation of nitrosugars into branched chain iminosugars: synthesis of 1,4-dideoxy-4-C-hydroxymethyl-1,4-imino-pentanols.

A novel promising strategy for the transformation of nitrosugars into branched pyrrolidines, based on double Henry reaction with formaldehyde followed by reductive ring closure, allowed the first enantiospecific synthesis of a 4-C-hydroxymethyl branched derivative of the well-known glycosidase inhib...

Bibliografski detalji
Glavni autori:	Otero, J, Soengas, R, Estévez, J, Estévez, R, Watkin, D, Evinson, E, Nash, R, Fleet, G
Format:	Journal article
Jezik:	English
Izdano:	2007

Slični predmeti

Hydroxymethyl-Branched Piperidines from Hydroxymethyl-Branched Lactones: Synthesis and Biological Evaluation of 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-mannitol, 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-L-gulitol and 1,5-Dideoxy-2-C-hydroxymethyl-1,5-imino-D-talitol
od: Soengas, R, i dr.
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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
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Izdano: (2008)

POTENT COMPETITIVE-INHIBITION OF ALPHA-GALACTOSIDASE AND ALPHA-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS - SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL
od: Fleet, G, i dr.
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Looking glass inhibitors: synthesis of a potent naringinase inhibitor L-DIM [1,4-dideoxy-1,4-imino-L-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-D-mannitol] a potent alpha-D-mannosidase inhibitor
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Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol.
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THE SYNTHESIS FROM D-XYLOSE OF THE POTENT AND SPECIFIC ENANTIOMERIC GLUCOSIDASE INHIBITORS, 1,4-DIDEOXY-1,4-IMINO-D-ARABINITOL AND 1,4-DIDEOXY-1,4-IMINO-L-ARABINITOL
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INHIBITION OF ALPHA-MANNOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL
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An alpha-glucoside of 1,4-dideoxy-1,4-imino-D-lyxitol with an eleven carbon side chain
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1,4-Dideoxy-1,4-imino-D-mannitol inhibits glycoprotein processing and mannosidase.
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3,6-dideoxy-3,6-imino-1,2-o-isopropylidene-α-d-glucofuranose as a divergent intermediate for the synthesis of hydroxylated pyrrolidines; synthesis of 1,4 dideoxy-1,4-imino-l-gulitol,...
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Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol [a potent competitive inhibitor of alpha-D-galactosidase] and of 1,4-dideoxy-1,4-imino-L-lyxitol [a weak competitive inhibitor of alpha-D-galactosidase] inhibit naringinase, an alpha-L-rhamnosidase competitively
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Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose
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DESIGN SYNTHESIS AND PRELIMINARY EVALUATION OF A POTENT ALPHA-MANNOSIDASE INHIBITOR - 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL
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Effects of the alpha-mannosidase inhibitors, 1,4-dideoxy-1,4-imino-D-mannitol and swainsonine, on glycoprotein catabolism in cultured macrophages.
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Izdano: (1989)

Crystal structure of 1,4-dideoxy-1,4-imino-D-gulitol hydrochloride, C6H14CINO4
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Crystal structure of 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride, C6H14ClNO4
od: Henkel S., i dr.
Izdano: (1997-12-01)

Crystal structure of 1,4-dideoxy-1,4-imino-D-mannitol hydrochloride, C6H14ClNO4
od: Henkel S., i dr.
Izdano: (1997-12-01)

Crystal structure of 1,4-dideoxy-1,4-imino-D-gulitol hydrochloride, C6H14CINO4
od: Henkel S., i dr.
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3,6-DIDEOXY-3,6-IMINO-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE AS A DIVERGENT INTERMEDIATE FOR THE SYNTHESIS OF HYDROXYLATED PYRROLIDINES - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-L-GULITOL, 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL, 2S,3S,4R-3,4-DIHYDROXYPROLINE AND (1S,2R,8S,8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE [8-EPI-SWAINSONINE] - X-RAY CRYSTAL-STRUCTURE OF (1S,2R,8S,8AR)-1,2,8-TRIHYDROXY-5-OXO-OCTAHYDROINDOLIZINE
od: Austin, G, i dr.
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SYNTHESIS FROM D-LYXONOLACTONE OF 1,4-DIDEOXY-1,4-IMINO-L-ARABINITOL, A GLUCOSIDASE INHIBITOR WITH INVITRO ANTIVIRAL ACTIVITY
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Izdano: (1993)

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
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Enantiomeric 2-acetamido-1,4-dideoxy-1,4-iminoribitols as potential pyrrolidine hexosaminidase inhibitors
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Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol.
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3-O-Benzhydryl-2,5-dideoxy-2,5-imino-2-C-methyl-l-lyxono-1,4-lactone
od: David J. Watkin, i dr.
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2-Acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-L-ribitol
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Izdano: (2005)

SYNTHESIS OF THE ALPHA-MANNOSIDASE INHIBITORS SWAINSONINE [(1S, 2R, 8R, 8AR)-1,2,8-TRIHYDROXYOCTAHYDROINDOLIZINE] AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL FROM MANNOSE
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1,4-Dideoxy-1,4-imino‑d‑arabinitol (DAB) Analogues Possessing a Hydrazide Imide Moiety as Potent and Selective α‑Mannosidase Inhibitors
od: Marianne B. Haarr, i dr.
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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]
od: Fleet, G, i dr.
Izdano: (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]
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The synthesis of deoxygalactostatin and 2,6 imino-heptitol derivatives via stannane mediated hydroxymethylation of 5-azido-1,4-lactones
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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]
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SYNTHESIS OF THE MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND OF THE RING CONTRACTED SWAINSONINES, (1S, 2R, 7R, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE AND (1S, 2R, 7S, 7AR)-1,2,7-TRIHYDROXYPYRROLIZIDINE
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2-Acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-L-arabinitol 0.33-hydrate
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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]
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2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride-oxy-l-xylitol (N-benzyl-l-XYLNAc).
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3-O-tert-butyldimethylsilyl-2,2 ': 5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-1,4-gluconolactone
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N-Benzyl-1, 3-dideoxy-1, 3-imino-L-xylitol
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