An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones.

An approach to 8 stereoisomers of homonojirimycin from (D)-glucose via kinetic and thermodynamic azido-γ-lactones.

Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements o...

Full description

Bibliographic Details
Main Authors:	Glawar, A, Jenkinson, S, Newberry, S, Thompson, A, Nakagawa, S, Yoshihara, A, Akimitsu, K, Izumori, K, Butters, T, Kato, A, Fleet, G
Format:	Journal article
Language:	English
Published:	2013

Similar Items

Eight stereoisomers of homonojirimycin from D-mannose.
by: Lenagh-Snow, G, et al.
Published: (2012)

Homonojirimycin isomers and N-alkylated homonojirimycins: structural and conformational basis of inhibition of glycosidases.
by: Asano, N, et al.
Published: (1998)

6-Azido-6-de-oxy-α-l-galactose (6-azido-l-fucose) monohydrate.
by: Booth, K, et al.
Published: (2008)

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.
by: Araújo, N, et al.
Published: (2012)

Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols.
by: Crabtree, E, et al.
Published: (2014)

Attempted ring contraction of α-triflates of 3-azido- and 3-fluoro-γ-lactones to oxetanes
by: Elliott, R, et al.
Published: (1990)

Attempted ring contraction of α-triflates of 3-azido- and 3-fluoro-γ-lactones to oxetanes
by: Elliot, R, et al.
Published: (1990)

3-Hydroxyazetidine carboxylic acids: non-proteinogenic amino acids for medicinal chemists.
by: Glawar, A, et al.
Published: (2013)

6-Azido-6-deoxy-α-l-galactose (6-azido-l-fucose) monohydrate
by: Sarah F. Jenkinson, et al.
Published: (2008-08-01)

2-Azido-3,4;6,7-di-O-isopropyl-idene-α-d-glycero-d-talo-heptopyran-ose.
by: Jenkinson, S, et al.
Published: (2010)

2-azido-2-deoxy-2,4-C-dimethyl-3,4-O-isopropylidene-L-ribono-1,5-lactone
by: Booth, K, et al.
Published: (2007)

Homonojirimycin analogues and their glucosides from Lobelia sessilifolia and Adenophora spp. (Campanulaceae).
by: Ikeda, K, et al.
Published: (2000)

ATTEMPTED RING CONTRACTION OF ALPHA-TRIFLATES OF 3-AZIDO-GAMMA-LACTONES AND 3-FLUORO-GAMMA-LACTONES TO OXETANES
by: Elliott, R, et al.
Published: (1990)

Short and sweet: (D)-glucose to (L)-glucose and (L)-glucuronic acid.
by: Martínez, R, et al.
Published: (2014)

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

2-Azido-2-de-oxy-3,4-O-isopropyl-idene-2-C-methyl-d-talono-1,5-lactone.
by: Jenkinson, S, et al.
Published: (2010)

2-Azido-2-deoxy-3,4-O-isopropylidene-2-C-methyl-d-talono-1,5-lactone
by: Sarah F. Jenkinson, et al.
Published: (2010-05-01)

Chromatographic lipophilicity and pharmacokinetic behavior of some newly synthesized styryl lactone stereoisomers
by: Lоnčаr Dаvоr М., et al.
Published: (2017-01-01)

The synthesis of deoxygalactostatin and 2,6 imino-heptitol derivatives via stannane mediated hydroxymethylation of 5-azido-1,4-lactones
by: Shilvock, J, et al.
Published: (1998)

Piperidine analogues of D-galactose as potent inhibitors of alpha-galactosidase: Synthesis by stannane-mediated hydroxymethylation of 5-azido-1,4-lactones. Structural relationships between D-galactosidase and L-rhamnosidase inhibitors
by: Shilvock, J, et al.
Published: (1999)

Conversion of L-rhamnose into ten of the sixteen 1-and 6-deoxyketohexoses in water with three reagents: D-tagatose-3-epimerase equilibrates C3 epimers of deoxyketoses
by: Gullapalli, P, et al.
Published: (2010)

2-Azido-3,4;6,7-di-O-isopropylidene-&#945;-d-glycero-d-talo-heptopyranose
by: Amber L. Thompson, et al.
Published: (2010-03-01)

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]
by: Hotchkiss, D, et al.
Published: (2007)

Structural essentials for β-N-acetylhexosaminidase inhibition by amides of prolines, pipecolic and azetidine carboxylic acids
by: Glawar, A, et al.
Published: (2016)

2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride-oxy-l-xylitol (N-benzyl-l-XYLNAc).
by: Jenkinson, S, et al.
Published: (2010)

Templated scaffolds of cis- and trans-tetrahydrofuran gamma-amino acids: gamma-azido-beta-hydroxy-tetrahydrofuran-2-carboxylates from pentono-delta-lactones
by: Sanjayan, G, et al.
Published: (2003)

Synthesis of eight stereoisomers of pochonicine: nanomolar inhibition of β-N-acetylhexosaminidases.
by: Zhu, J, et al.
Published: (2013)

Direct production of L-tagatose from L-psicose by Enterobacter aerogenes 230S.
by: Rao, D, et al.
Published: (2008)

ALPHA-HOMONOJIRIMYCIN [2,6-DIDEOXY-2,6-IMINO-D-GLYCERO-L-GULO-HEPTITOL] FROM OMPHALEA-DIANDRA L - ISOLATION AND GLUCOSIDASE INHIBITION
by: Kite, G, et al.
Published: (1988)

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
by: Baird, P, et al.
Published: (1987)

3-azido-3-deoxy-2,2 ': 5,6-di-O-isopropylidene-2-C-hydroxmethyl-D-gulono-1,4-lactone
by: Harding, C, et al.
Published: (2004)

d-Idose, d-Iduronic Acid, and d-Idonic Acid from d-Glucose via Seven-Carbon Sugars.
by: Liu, Z, et al.
Published: (2019)

6-Azido-3-O-benzyl-6-deoxy-N, N-diethyl-1, 2-O-isopropylidene-D-glycero-α-D-gluco-heptofuranuronamide
by: Jenkinson, S, et al.
Published: (2011)

(2S,4S)-4-azido-1-benzyl-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl] pyrrolidine
by: Chesterton, A, et al.
Published: (2006)

2-C-Benzyloxymethyl-2,3 : 5,6-di-O-isopropylidene-D-allono-1,4-lactone
by: Watkin, D, et al.
Published: (2005)

2,6-Dide-oxy-2,6-imino-l-glycero-d-ido-heptitol.
by: Jenkinson, S, et al.
Published: (2009)

A versatile kinetic alkylation-ozonolysis route for the synthesis of lactones: chiral γ-lactones and racemic δ-lactones
by: Niall W.A. Geraghty, et al.
Published: (2003-05-01)

1-De-oxy-d-galactitol (l-fucitol).
by: Jenkinson, S, et al.
Published: (2008)

6-Azido-3-O-benzyl-6-de-oxy-N,N-diethyl-1,2-O-isopropyl-idene-d-glycero-α-d-gluco-heptofuran-uronamide.
by: Jenkinson, S, et al.
Published: (2010)

Looking-glass synergistic pharmacological chaperones: DGJ and L-DGJ from the enantiomers of tagatose.
by: Jenkinson, S, et al.
Published: (2011)