- Regiospecific formation of sugar-derived ketonitrone towards unconventional: C -branched pyrrolizidines and indolizidines
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The synthesis of unprecedented branched pyrrolizidines and indolizidines was accomplished via nitrone chemistry. The required ketonitrone, a known intermediate usually obtained as a mixture of regioisomers, was prepared in a pure form from d-arabinose by
- Massicot, Fabien,Messire, Gatien,Vallée, Alexis,Vasse, Jean-Luc,Py, Sandrine,Behr, Jean-Bernard
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p. 7066 - 7077
(2019/08/01)
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- A practical approach to Dideoxy-1,4- and 1,5-iminopentitols from protected sugar hemiacetals
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The convenient and straightforward preparation of dideoxy-1,4- and 1,5-iminopentitol derivatives from protected sugar hemiacetals by way of N-tert-butanesulfinyl glycosylamines and open-chain aminoalditols is reported. The synthetic procedure is a method of choice for the making of these important scaffolds of biological interest.
- Jaszczyk, Justyna,Li, Sizhe,Cocaud, Chloé,Nicolas, Cyril,Martin, Olivier R.
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- A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol using Co(III)(salen)-catalyzed hydrolytic kinetic resolution of a two-stereocentered anti-azido epoxide
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A concise enantioselective synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol, (+)-DAB-1, has been described in good overall yield (18.1%) and with high enantiomeric purity (up to 98% ee) starting from a simple raw material, cis-2-butene-1,4-diol. The Co-catalyzed hydrolytic kinetic resolution of a two-stereocentered racemic azido epoxide followed by asymmetric dihydroxylation of the alkene and ‘one pot’ reductive cyclisation of the azido diol are key reactions in the synthetic sequence.
- Reddi, Rambabu N.,Prasad, Pragati K.,Kalshetti, Rupali G.,Sudalai, Arumugam
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p. 162 - 165
(2017/01/10)
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- Synthesis and Evaluation of Hybrid Structures Composed of Two Glucosylceramide Synthase Inhibitors
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Glucosylceramide metabolism and the enzymes involved have attracted significant interest in medicinal chemistry, because aberrations in the levels of glycolipids that are derived from glucosylceramide are causative in a range of human diseases including lysosomal storage disorders, type2 diabetes, and neurodegenerative diseases. Selective modulation of one of the glycoprocessing enzymes involved in glucosylceramide metabolism - glucosylceramide synthase (GCS), acid glucosylceramidase (GBA1), or neutral glucosylceramidase (GBA2) - is therefore an attractive research objective. In this study we took two established GCS inhibitors, one based on deoxynojirimycin and the other a ceramide analogue, and merged characteristic features to obtain hybrid compounds. The resulting 39-compound library does not contain new GCS inhibitors; however, a potent (200nm) GBA1 inhibitor was identified that has little activity toward GBA2 and might therefore serve as a lead for further biomedical development as a selective GBA1 modulator. Taking the best of both: Two established glucosylceramide synthase (GCS) inhibitors were merged via convergent synthesis to obtain hybrid compounds. Members of this 39-compound library have characteristics of both parent GCS inhibitors. No new GCS inhibitors were established, but a potent (200nm) acid glucosylceramidase (GBA1) inhibitor was identified. This adamantanemethyloxypenanoic acid pyrrolidene-substituted derivative of eliglustat can serve as a lead for further biomedical development of selective GBA1 modulators.
- Vandenberg, Richard J.B.H.N.,Vanrijssel, Erwin R.,Ferraz, Maria Joao,Houben, Judith,Strijland, Anneke,Donker-Koopman, Wilma E.,Wennekes, Tom,Bonger, Kimberly M.,Ghisaidoobe, Amar B. T.,Hoogendoorn, Sascha,Vandermarel, Gijsbert A.,Codée, Jeroen D. C.,Overkleeft, Herman S.,Aerts, Johannes M. F. G.
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p. 2042 - 2062
(2015/12/23)
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- A versatile approach to N-alkylated 1,4-dideoxy-1,4-imino-d-arabinitols and 1,4-dideoxy-1,4-imino-l-xylitols
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A versatile and concise synthesis of N-alkylated 1,4-dideoxy-1,4-imino-d- arabinitol and 1,4-dideoxy-1,4-imino-l-xylitol derivatives is described. These were prepared using pseudohemiketal lactams as key intermediates, which in turn were obtained from suc
- Wang, Guan-Nan,Yang, Lin,Zhang, Li-He,Ye, Xin-Shan
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experimental part
p. 2001 - 2009
(2011/06/20)
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- Synthesis of naturally occurring iminosugars from d-fructose by the use of a zinc-mediated fragmentation reaction
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A short synthesis of 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) and a formal synthesis of australine are described. In both cases, d-fructose is employed as the starting material and converted into a protected methyl 6-deoxy-6-iodo- furanoside. Zinc-mediate
- Lauritsen, Anne,Madsen, Robert
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p. 2898 - 2905
(2008/02/09)
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- Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: Total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine
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The total syntheses of DAB1 (1) and (-)-lentiginosine (2) were concisely accomplished from D-lyxose via regioselective and diastereoselective NHCbz introduction using CSI, chemoselective removal of the Cbz protection, and ring-closing metathesis as key steps.
- Kim, In Su,Zee, Ok Pyo,Jung, Young Hoon
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p. 4101 - 4104
(2007/10/03)
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- NEW SALT OF (2R,3R,4R)-3,4-DIHYDROXY-2-HYDROXYMETHYLPYRROLIDINE
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This invention relates to (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine, 2-naphthalenesulfonate, preparation thereof and use as therapeutic agent.
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Page/Page column 8
(2008/06/13)
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- Salt of (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine
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A new salt of (2R,3R,4R)-3,4-dihydroxy-2-hyroxymethylpyrrolidine is disclosed. Specifically, (2R,3R,4R-3,4-dihydroxy-2-hydroxymethylpyrrolidine, 2-naphthalenesulfonate is disclosed, as well as its preparation and use for treating and preventing diabetes a
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- Stereoselective synthesis of (+)-1,8-Di-epi- and (-)-1-epi-swainsonine from an (S)-pyroglutamic acid derivative
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(+)-1,8-Di-epi-swainsonine (15) and (-)-1-epi-swainsonine (17) were synthesized stereoselectively from an (S)-pyroglutamic acid derivative (1a). A (2R,3R,4R)-3,4-dihydroxy-2-hydroxymethylpyrrolidine derivative (6a) was prepared by cis-dihydroxylation of a
- Ikota
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p. 1717 - 1721
(2007/10/02)
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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-AMINO-L-ARABINITOL
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Both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol are specific inhibitors of glucosidases.The synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol involves connecting C2 and C5 of xylose together with nitrogen, whereas the synthesis of 1,4-dideoxy-1,4-imino-
- Fleet, George W. J.,Smith, Paul W.
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p. 5685 - 5692
(2007/10/02)
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