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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of Hetaryl Glycosides and Their Glycosyl Donor Properties (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1353-1360 
    Details
    ISSN: 1434-193X
    Keywords: Heterocycles ; Substitution ; Carbohydrates ; Anomeric O-hetarylation ; Glycosylation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Anomeric O-hetarylation of tetra-O-benzyl- and tetra-O-acetylglucose (1a, b) can be directly performed with electron-deficient heteroaromatic/heterocyclic systems 2-14, which contain imide halide moieties. The reactions were carried out in the presence of a base and led, through an exchange of the halide by the glucopyranosyloxy moiety, to the products 2a-14a, 7b-14b. Predominantly or exclusively β-products were obtained. Systems bearing more than one imide halide moiety, such as cyanuric fluoride (15) or 5-chloro-2,4,6-trifluoropyrimidine (16), can be employed for successive anomeric O-hetarylations. Investigation of the glycosyl donor properties of O-glucosyl heteroaromatic imidates with 6-O- and 4-O-unprotected glucose derivatives 18 and 19 as acceptors and comparison of the results obtained with data for the corresponding β-trichloroacetimidates 17aβ and 17bβ, reveals that 2,3,5,6-tetrafluoropyridin-4-yl glucopyranosides 14aβ and 14bβ exhibit similar properties. For specific tasks, for instance α-glucopyranoside formation, 14aβ may even be advantageous.
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  • 2
    Electronic Resource
    Electronic Resource
    Syntheses and Properties of S2-Bridged Benzidines (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 2409-2416 
    Details
    ISSN: 1434-193X
    Keywords: Sulfur heterocycles ; Rearrangements ; Reductions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The syntheses of 1,2-benzodithiino[5,4,3-cde][1,2]benzodithiin-2,7-diamine (1) and dithio-bridged benzidine 2 have been achieved. The starting material for the synthesis of 1 was 1,3-diiodo-5-nitrobenzene (15) which was transformed by conventional means into 1,2-bis[3,5-bis(ethylthio)phenyl]diazane (19). The benzidine rearrangement of 19 in the presence of HBF4 at -30 °C yielded 4,4′-diamino-2,2′,6,6′-tetraethylthiobiphenyl (20) in 50 % yield. Treatment of 20 with sodium in ammonia and work-up in the presence of air yielded 1. The latter compound could be reduced with LiAlH4 to the tetrathiol 20a. The starting material for the preparation of 2 was 3-chloro-1-iodo-5-nitrobenzene (23), a side product of the preparation of 15. It was transformed analogously to the preparation of 1 into 1,2-bis(3-ethylthiophenyl)diazane (28). The benzidine rearrangement of 28 in presence of HBF4 at -30 °C afforded 4,4′-diamino-2,2′-bis(ethylthio)biphenyl (29) in 49 % yield. Treatment of 29 with sodium in ammonia and work-up under aerobic conditions yielded 2. Quantitative reduction of 2 to the thiol 29a could be achieved with LiAlH4. The reversible electrochemical reduction of 1 on unmodified glassy carbon electrodes leads to a product to which the structure of 3 was assigned.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Polar and Steric Substituent Effects in 5-exo-trig Cyclizations of 1-Aryl-4-penten-1-oxyl Radicals (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 523-523 
    Details
    ISSN: 1434-193X
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -By mistake wrong concentrations were given in the footnote of Table 1 and in the Discussion. Instead of c0 = 1.2 M read c0 = 0.12 M if 2-naphthalenethiol was used as hydrogen donor and instead of c0 = 1.8 M read c0 = 0.18 M if Bu3SnH was used to trap photoproducts. In Table 2 relative rate constants of radical 2d refer to radical 2e and vice versa as correctly stated in the Discussion. In the Experimental Section (Iodocyclization) read 2.25 g (8.86 mmol) of iodine instead of 2.25 g (1.10 mmol) of iodine.
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  • 4
    Electronic Resource
    Electronic Resource
    A Novel and Efficient Route towards α-GalNAc-Ser and α-GalNAc-Thr Building Blocks for Glycopeptide Synthesis (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1167-1171 
    Details
    ISSN: 1434-193X
    Keywords: Carbohydrates ; Glycals, nitro ; Michael additions ; Glycosylations ; Glycosides, galactosamine ; Reduction, nitro group ; Glycopeptides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Michael addition of serine and threonine derivatives 4a-4c to 3,4,6-tri-O-benzyl-2-nitro-D-galactal (1) afforded the corresponding 2-deoxy-2-nitro-α-D-galactopyranosides 5a-5c in good yield and stereoselectivity. 2-deoxy-2-nitroglycosides 5a and 5b were reduced to the 2-acetamido compounds by platinized Raney nickel T4. Manipulation of the protecting groups afforded known N-Fmoc-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine (8a) and -threonine (8b), valuable building blocks for O-glycopeptide synthesis.
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  • 5
    Electronic Resource
    Electronic Resource
    Synthesis of a Central Intermediate in the Biosynthesis of Di- and TrideoxysugarsDedicated to Professor Gottfried Huttner on the occasion of his 60th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1907-1914 
    Details
    ISSN: 0947-3440
    Keywords: Nucleoside diphosphate sugars, synthesis ; Biosynthesis ; Deoxysugars ; Glycosyl phosphites ; Glycosyl phosphates ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of disodium (6-deoxy-α-D-ribo-hexopyran-3-ulosyl) (2′-deoxythymidin-5′-yl) diphosphate (1) is described. To this end, D-glucose is transformed into known furanose derivative 2 possessing a 3-C-methylene group as latent functionality for 3-ulose generation. From 2, 3,6-dideoxy derivative 6 was synthesized; ensuing acid catalyzed cleavage of the 1,2-O-isopropylidene group and then O-acetylation furnished the required pyranose 8α,β, which could be selectively deacetylated at the anomeric oxygen to afford 9α,β. Treatment with phosphitylating agent 13e and then oxidation led to dibenzylphosphate derivative 15e which could be chemoselectively debenzylated by hydrogenolysis without affecting the olefinic double bond (→ 17); de-O-acetylation and then ozonolysis afforded the unprotected phosphate intermediates 18 and 19, respectively. Both compounds could be successfully used for the synthesis of 1 by employing the nucleoside phosphate morpholidate procedure for the generation of nucleoside diphosphate sugars. Ozone cleavage of the olefinic double bond in 20 could be successfully performed even in the presence of the thymine moiety.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970916
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis of Thio-Linked Analogues of Lewis X and Sialyl Lewis XDedicated to Professor Hans Paulsen on the occasion of his 75th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1303-1313 
    Details
    ISSN: 0947-3440
    Keywords: S-Glycosylation, base-promoted, acid-catalyzed ; S-Glycosides ; Anomeric S-alkylation ; Glycosyltrichloroacetimidates ; Lewis X analogues ; Oligosaccharides, thio- ; Carbohydrates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of thio-linked Lewis X and sialyl Lewis X-derived epitopes 3-5 has been achieved using a small number of building blocks. The key building-block was 1-O-silyl-protected 4-S-acetyl-2,6-di-O-benzoyl-3-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-3,4-dithio-β-D-glucopyranose (15), which was obtained from the fucosyl donor 6 together with 3-thiogalactose 7 as the acceptor. Their acid-catalyzed S-glycosylation afforded the thio-linked disaccharide 8 which was subsequently converted to the 4a-O-unprotected derivative 12. Conversion to the 4a-triflate followed by treatment with KSAc in tetrahydrofuran led, under inversion of configuration, to 15 in good overall yield. Selective removal of the S-acetyl group followed by base-promoted S-glycosylation with acetobromogalactose gave the acyl-protected Lewis X analogue 25. Acetobromogalactose gave the acyl-protected Lewis X analogue 25. Transformation into trichloroacetimidate 27, followed by acid-catalyzed S-glycosylation of heptylthiol and complete deacylation afforded target molecule 3. Similarly, acid-catalyzed reaction of donor 27 and the 3b,4b-O-unprotected lactose derivative 31 as acceptor led to pentasaccharide 32, complete deacylation of which afforded target molecule 4. Transformation of 15 into the donor trichloroacetimidate 34, followed by acid-catalyzed S-glycosylation of heptylthiol afforded thioglycoside 35. Selective removal of the S-acetyl group and subsequent base-promoted S-glycosylation with the known donor 37 furnished the thio-linked tetrasaccharide 38. Cleavage of all the O-acyl groups and hydrolysis of the methyl ester moiety afforded the sialyl Lewis X analogue 5.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970705
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  • 7
    Electronic Resource
    Electronic Resource
    C-Disaccharides of Ketoses (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 502-510 
    Details
    ISSN: 0947-6539
    Keywords: alkynes ; C-glycosides ; cobalt complexes ; cyclizations ; enzyme inhibitors ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of gluconolactone 2 with allylmagnesium bromide at low temperatures afforded ketopyranose 3, which could easily be converted into open-chain ketoses (R)-6 and (S)-6. Their reaction with lithioacetylide 9 afforded propargylic alcohol derivatives (R)-10 and (S)-10, which could not be cyclized directly to the desired C-ketosides. They were converted by standard procedures into (R)-14 and (S)-14 and then into dicobalthexacarbonyl complexes (R)-16 and (S)-16. A facile acid-catalyzed ring closure gave the desired C-ketosides (R)-18 α/β and (S)-18α/β, respectively, in different ratios. In order to demonstrate that removal of the protective groups and hydrogenation of the CC triple bond proceed smoothly, (R)-18 α was transformed into the deprotected target molecule (R)-1 α. For the assignment of the new chiral centers at C-2/2′ and at C-8, (S)-18α was transformed into azido derivative (S)-22α, which underwent intramolecular cycloaddition to afford the spiro derivative (S)-25α. Because of the conformational constraints in this molecule, unequivocal configurational assignment was possible with the help of NMR data.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19960020508
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  • 8
    Electronic Resource
    Electronic Resource
    Photoreactions of phenyl-substituted N-(pent-4-enyl-1-oxy)pyridine-2(1 H)-thiones (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 1014-1023 
    Details
    ISSN: 0947-6539
    Keywords: alkoxy radicals ; cyclizations ; pyridinethiones ; radicals ; tetrahydrofurans ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of hitherto unknown N-(pent-4-enyl-1-oxy)pyridine-2(1 H)-thiones (6) were prepared from substituted pent-4-enyl tosylates or benzylic chlorides. On irradiation with incandescent light heterocycles 6 liberated alkoxy radicals 2, which were studied for rearrangement reactions. Surprisingly, all transformations involving the 1-phenylpent-4-enyl-1-oxy radical (2a), for example, to give the substituted thioether 8, 2-bro-momethyl-5-phenyltetrahydrofuran (11), or the tetrahydrofuran 14a, were not stereoselective. On the other hand 2-, 3- mono-, and 1,5-disubstituted pent-4-enyl-1-oxy radicals 2d-e and 2g cyclized in good yields and with good to excellent stereoselectivities to give the corresponding 2,4-cis- and 2,3-trans-phenyltetra-hydrofurfuryl radicals 3d-e, and the trans-2-benzyl-5-methyl substituted intermediate 3g. The major reaction mode of the 4-phenylpent-4-enyl-1-oxy radical (2f) was the 6-endo cyclization, which afforded 3-phenyltetrahydropyran (13f) as the major product (endo:exo = 93:7) after trapping with hydrogen donors. According to the experimental data of the present study, the unusual reactivity of the 1-phenylpent-4-enyl-1-oxy radical (2a) in 5-exo-trig ring closures could be caused by a coplanar arrangement of the benzyloxy moiety in the transition state of the cyclization. This interaction would lock the radical center in 2a in a preferred conformation, which would result in similar steric effects for both cis- and trans- cyclizations.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.1460020816
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  • 9
    Electronic Resource
    Electronic Resource
    Asymmetric Control in the Pictet-Spengler Reaction by Means of N-Protected Amino Acids as Chiral Auxiliary Groups (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 1566-1571 
    Details
    ISSN: 0947-6539
    Keywords: amino acids ; asymmetric syntheses ; carbolines ; chiral auxiliaries ; Pictet-Spengler reaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Aromatic and aliphatic Schiff bases of tryptamine react with Fmoc- or phthaloyl-protected amino acid chlorides to form N-acyliminium intermediates, which, in the presence of titanium alkoxides at room temperature, undergo Pictet-Spengler reactions to give tetrahydro-β-carbolines with diastereomeric ratios of up to 99:1. The chiral auxiliary can be removed from the Pictet-Spengler adducts by means of a simple reduction. To rationalize the observed stereoselectivity a transition-state model is proposed in which the titanium atom coordinates both the carbonyl group of the N-acyliminium ion and the amino acid protecting group.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19960021215
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  • 10
    Electronic Resource
    Electronic Resource
    The Aluminum-Nitrogen Bond in Monomeric Bis(amino)alanes: A Systematic Experimental Study of Bis(tetramethylpiperidino)alanes and Quantum Mechanical Calculations on the Model System (H2N)2AlY (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 1095-1114 
    Details
    ISSN: 1434-1948
    Keywords: Aminoalanes ; Alanes ; Ab initio calculations ; 27Al-NMR spectroscopy ; Structure elucidation ; Substituent effects ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of metallated nucleophiles MIY [Y = OR, SR, NR2, PR2, AsR2, CR3, Si(SiMe3)3, R = organyl, H] with bis(2,2,6,6-tetramethylpiperidino)aluminum halides [tmp2AlX, (X = Cl, Br, I)] offer facile access to a variety of bis(amino)alanes of the type tmp2AlY. As indicated by 27Al-NMR spectroscopy, mass spectrometry and X-ray crystal structure determina-tions, all of these compounds are monomeric in the solid state, in solution, and in the gas phase. Even Al-E single bonds (E = Si, P, As etc.) that are not commonly encountered are stabilized by the supporting tmp fragments. The results of a systematic analysis of the bonding parameters determined for the tmp2AlY compounds, combined with a quantum mechanical study on model compounds (H2N)2AlY, not only reveal the presence of a highly polar Al-N bond, but at the same time rule out AlN-pp(π) bonding, in contrast to the situation in the analogous tmp2BY compounds. It is shown that the Al-N bond length depends on the acidic character of the protic species HY: the shorter d(Al-N), the less basic is Y.
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