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

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

The first stereocontrolled synthesis of (3R,4R,5R,6S)-2,2-bis-(hydroxymethyl)azepane-3,4,5,6-tetraol is described herein. The method involves a novel double Henry reaction of the 3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-d-glucofuranose with formaldehyde followed by a reductive ring clo...

Full description

Bibliographic Details
Main Authors:	Otero, J, Estevez, A, Soengas, R, Estevez, J, Nash, R, Fleet, G, Estevez, R
Format:	Journal article
Language:	English
Published:	2008

Similar Items

Preliminary studies on the transformation of nitrosugars into branched chain iminosugars: synthesis of 1,4-dideoxy-4-C-hydroxymethyl-1,4-imino-pentanols.
by: Otero, J, et al.
Published: (2007)

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
by: Simone, M, et al.
Published: (2012)

3,6-Dichlorobenzene-1,2,4,5-tetraol
by: R. Alan Aitken, et al.
Published: (2022-07-01)

General synthesis of sugar-derived azepane nitrones: precursors of azepane iminosugars.
by: Zhao, W, et al.
Published: (2013)

2-r-(4-Chlorophenyl)-6-c-phenyl-3,4,5,6-tetrahydro-2H-thiopyran-4-one 1-oxide
by: D. Devanathan, et al.
Published: (2008-12-01)

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]
by: Nash, R, et al.
Published: (1988)

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
by: Nash, R, et al.
Published: (1988)

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]
by: Edgeley, D, et al.
Published: (2012)

Cyclohexanaminium 3,4,5,6-tetrachloro-2-(methoxycarbonyl)benzoate
by: Jian Li
Published: (2011-04-01)

3-O-tert-butyldimethylsilyl-2,2 ': 5,6-di-O-isopropylidene-2-C-hydroxymethyl-D-1,4-gluconolactone
by: Cowley, A, et al.
Published: (2004)

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)

(3R,4S,5R,6R,7S)-3,4,5,7-Tetrahydroxyconidine, an azetidine analogue of 6,7-diepicastanospermine and a conformationally constrained d-deoxyaltronojirimycin, from l-arabinose.
by: Martínez, R, et al.
Published: (2013)

Crystal structure of (1S,3R,4R,5S,6R)-4-0-benzyl-4.5-dihydroxy-3-hydroxymethyl- 2,7-dioxabicyclo-[4.3.0]nonan-8-on, C15H18O6
by: Henkel S., et al.
Published: (1997-12-01)

Crystal structure of (1S,3R,4R,5S,6R)-4-0-benzyl-4.5-dihydroxy-3-hydroxymethyl- 2,7-dioxabicyclo-[4.3.0]nonan-8-on, C15H18O6
by: Henkel S., et al.
Published: (1997-12-01)

2S,3R,4R,5S)-3,4,5-trihydroxypipecolic acid dihydrate [(2S,3R,4R,5S)-3,4,5-tri-hydroxypiperidine-2-carboxylic acid dihydrate]
by: Booth, K, et al.
Published: (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
by: Punzo, F, et al.
Published: (2006)

(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].
by: Best, D, et al.
Published: (2009)

Heptaaqua(3,4,5,6-tetrachlorophthalato-&#954;O1)erbium(III) 2-carboxy-3,4,5,6-tetrachlorobenzoate&#8211;3,4,5,6-tetrachlorophthalic acid&#8211;water (1/1/1)
by: Yan Ouyang, et al.
Published: (2012-05-01)

(R)-7-(Azepan-3-ylamino)-8-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic Acid Hydrochloride
by: Shuitao Yu, et al.
Published: (2013-05-01)

Crystal structure of (3aR,5S,6R,6aR)-6-hydroxy-5-hydroxymethyl-perhydrofuro[3,2-b]furan-2-one, C7H10O5
by: Frey W., et al.
Published: (1999-06-01)

(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.
by: Jenkinson, S, et al.
Published: (2009)

Steviamine, a new class of indolizidine alkaloid [(1R,2S,3R,5R,8aR)-3-hydroxymethyl- 5-methyloctahydroindolizine-1,2- diol hydrobromide]
by: Thompson, A, et al.
Published: (2009)

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
by: Soengas, R, et al.
Published: (2012)

(1R,3S,5R,6S)-6-Acetoxy-3-(4-methylphenylsulfonyloxy)tropane
by: Yang Lu, et al.
Published: (2008-12-01)

Crystal structure of (2S,4R,5R,6R)-2-(4,5-dibenzyloxy-6-benzyloxymethyl tetrahydropyranyl)triphenylphosphonium tetrafluoroborate,α-C45H44PBF4O4 and of(2R,4R,5R,6R)-2-(4,5-dibenzyloxy-6-benzyloxy-methyl tetrahydropyranyl)triphenylphosphonium tetrafluoroborate, β-C45H44PBF4O4
by: Frey W., et al.
Published: (1998-04-01)

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
by: Bashyal, B, et al.
Published: (1986)

Crystal structure of 3S,4S,5R,6S,7R-5-amino-6-(tert-butyldimethylsiloxy)-7- (tert-butyldimethylsiloxymethyl)-3-hydroxymethyl-2,2-dimethyloxepan-4-ol, C22H49NO5Si2
by: AI-Hanasi A., et al.
Published: (2006-04-01)

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.
by: Jenkinson, S, et al.
Published: (2009)

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

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
by: Bashyal, B, et al.
Published: (1987)

Crystal structure of tert-butyl (1S,2R,5R)-2-(hydroxymethyl)-4-(4-methoxyphenyl)-6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate, C17H23NO5
by: Caracelli Ignez, et al.
Published: (2020-10-01)

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

Low-temperature redetermination of 3,4,5,6-tetra-hydro-pyrimidin-2(1H)-one.
by: Rizal, M.R., et al.
Published: (2008)

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

A Corey lactone: crystal structure of (3aR,4R,5R,6aS)-5-benzoyloxy-4(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one, C15H16O5
by: Wang Kun-Yan, et al.
Published: (2018-01-01)

Ethyl (3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-3-{(3S)-3-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[4,5-d][1,3]dioxol-5-yl]-5-oxoisoxazolidin-2-yl}propanoate chloroform monosolvate
by: Aldo Guillermo Amaro Hernández, et al.
Published: (2020-06-01)

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

A concise synthesis of (5R,6S)-tert-butyl 5-acetoxy-6-(hydroxymethyl)-5,6-dihydropyridine-1(2H)-carboxylate
by: S. Ramalingam, et al.
Published: (2012-10-01)

Crystal structure of (2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((4aS,5R,6S)-1-oxo-5-vinyl-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl)oxy)tetrahydro-2H-pyran-3-yl 2,3-dihydroxybenzoate hydrate, C23H26O12·H2O
by: Zeng Xue, et al.
Published: (2024-04-01)

Asymmetric synthesis of 3,4,5,6-tetrasubstituted piperidin-2-ones by three-component coupling
by: Davies, S, et al.
Published: (2004)