- Synthesis of a novel UDP-carbasugar as UDP-galactopyranose mutase inhibitor
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The multistep synthesis of a novel UDP-C-cyclohexene, designed as a high energy intermediate analogue of the UDP-galactopyranose mutase (UGM) catalyzed isomerization reaction, is reported. The synthesis of the central carbasugar involved the preparation of a galactitol derivative bearing two olefins necessary for the construction of the cyclohexene ring by a ring-closing metathesis as a key step. Further successive phosphonylation, deprotection, and UMP coupling provided the target molecule. The final molecule was assayed against UGM and compared with UDP-C-Galf, the C-glycosidic UGM substrate analogue.
- El Bkassiny, Sandy,N'Go, Ines,Sevrain, Charlotte M.,Tikad, Abdellatif,Vincent, Stephane P.
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supporting information
p. 2462 - 2465
(2014/05/20)
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- A simple synthesis of D-galactono-1,4-lactone and key building blocks for the preparation of galactofuranosides
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The oxidation of D-galactose by Br2 to yield D-galactono-1,4-lactone was developed and applied to the preparation of key building blocks for the synthesis of galactofuranosides. Three D-galactono-1,4-lactone derivatives protected as acetates, TBDMS ether, or acetonide were directly obtained in two steps on multigram scale with only one purification step. A mild deacetylation methodology afforded pure D-galactono-1,4-lactone and a new reduction of the lactone functionality using K-selectride was also optimized.
- De Talance, Vincent Lemau,Thiery, Emilie,Eppe, Guillaume,Bkassiny, Sandy El,Mortier, Jeremie,Vincent, Stephane P.
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experimental part
p. 605 - 617
(2012/06/04)
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- δ-Galactonolactone: Synthesis, isolation, and comparative structure and stability analysis of an elusive sugar derivative
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δ-D-Gluconolactone, δ-D-mannonolactone, and - for the first time - the thermodynamically unstable δ-D-galactonolactone have been prepared and isolated from DMF solution by oxidizing the corresponding sugars with Shvo's catalyst [(C4Ph4CO)(CO)2Ru] 2 and a hydrogen acceptor. The preferred conformation of δ-D-galactonolactone in [D6] DMSO solution has been determined by 1H NMR spectroscopy experiments and DFT calculations to be 4H3 and is compared to those of the previously established conformations of δ-D-gluconolactone (4H3) and δ-D-mannonolactone (B2,5), The conformations of the lactones suggest an explanation for their relative rates of isomerization to their respective γ-D-lactones by an intramolecular mechanism. Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2004.
- Bierenstiel, Matthias,Schlaf, Marcel
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p. 1474 - 1481
(2007/10/03)
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- A new efficient access to glycono-1,4-lactones by oxidation of unprotected itols by catalytic hydrogen transfer with RhH(PPh3)4-benzalacetone system
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Treatment of unprotected pentitols and hexitols with RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones in 60-96% yield.
- Isaac,Aizel,Stasik,Wadouachi,Beaupère
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p. 475 - 476
(2007/10/03)
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- A NEW AND DIRECT ACCESS TO GLYCONO-1,4-LACTONES FROM GLYCOPYRANOSES BY REGIOSELECTIVE OXIDATION AND SUBSEQUENT RING RESTRICTION
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Treatment of partially protected or unprotected carbohydrates with the RhH(PPh3)4-benzalacetone system leads exclusively to glycono-1,4-lactones by regioselective oxidation and subsequent ring restriction.
- Isaac, Isabelle,Stasik, Imane,Beaupere, Daniel,Uzan, Raoul
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p. 383 - 386
(2007/10/02)
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- 2-Acetamido-2-deoxyaldonolactones from sugar formazans
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A new approach towards simple aldonic acid derivatives starting from the corresponding aldoses via the 2-acetamido-2-deoxy formazans resulted in the synthesis of 2-acetamido-2-deoxy-D-galactono-1,4-lactone (8), and its 6-deoxy (11) and 6-azido-6-deoxy (14) analogues on treatment with trifluoroacetic acid.The five-membered ring structure of the lactones and that of the intermediate lactone phenylhydrazone (7) was proved by 1H and 13C NMR studies, including deuterium-induced differential isotope shift (DIS) measurements.With sodium borohydride, lactones 8 and 11 were converted into 2-acetamido-2-deoxy-D-galactitol (15) and its 6-deoxy analogue (17), respectively.
- Zsoldos-Mady, Virag,Pinter, Istvan,Neszmelyi, Andras,Messmer, Andras,Perczel, Andras
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- Vitamin C and Isovitamin C Derived Chemistry. 2. Synthesis of Some Enantiomerically Pure 4,5,6-Trihydroxylated Norleucines
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A sequence leading to enantiomerically pure 4,5,6-trihydroxylated norleucines 23-25, their 5,6-O-isopropylidene derivatives 17a,b and 20, and lactones 19a,b and 22 from relatively inexpensive carbohydrate precursors is described. 5,6-O-Isopropylidene-L-gulono-, -D-mannono-, and -D-galactono-1,4-lactones (2a,b and 7b) react readily with 2 equiv of mesyl chloride in pyridine at 0 deg C to produce hex-2-enono-1,4-lactone 2-mesylates 5a,b and 8.The butenolides are stereoselectively reduced to 3-deoxyhexono-1,4-lactone 2-mesylates 11a,b and 12, which are then treated with sodium azide in DMF to generate the configurationally C-2-inverted azides 15a,b and 16.Hydrogenation thereof, in the presence of triethylamine, gives the 5,6-O-isopropylidenated title compounds 17a,b and 20, which are hydrolyzed in boiling water to give amino acids 23-25 and are converted into lactones 19a,b and 22 by treatment with dilute hydrochloric acid under reflux.The lactones are optimally produced directly from 15a,b and 16 by hydrogenation in the presence of acid.
- Vekemans, Jozef A. J. M.,Bruyn, Ronald G. M. de,Caris, Roberta C. H. M.,Kokx, Antonius J. P. M.,Konings, Jeroen J. H. G.,Godefroi, Erik F.
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p. 1093 - 1099
(2007/10/02)
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