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  • 1980-1984  (12)
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  • 1
    Electronic Resource
    Electronic Resource
    Specific photoaffinity inactivation of the D-glucose transporter in small intestinal brush border membrane using new phlorizin analogs (1981)
    s.l. : American Chemical Society
    Biochemistry 20 (1981), S. 5844-5854 
    Details
    ISSN: 1520-4995
    Source: ACS Legacy Archives
    Topics: Biology , Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/bi00523a030
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  • 2
    Electronic Resource
    Electronic Resource
    Desoxy-nitrozucker. 2. Mitteilung Herstellung geschützter 1-Desoxy-1-nitroaldosen (1982)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 65 (1982), S. 621-634 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Protected 1-Deoxy-1-nitroaldosesThe direct oxidation of the oxime 1 with t-butyl hydroperoxide and vanadyl acetylacetonate yielding the nitro derivative 2 (54%, Scheme 1) could not be applied to other oximes. Diastereoselective bromination of the aldonolactone oxims 7 and 10-12 according to known procedures gave the corresponding bromonitroso compounds which were oxidized to the bromonitro compounds 9, 14, 18 and 22, respectively. Oxidation of the bromonitroso compound in the D-mannopyranose series proved difficult, but the corresponding chloronitro derivative 23 was easily obtained according to Corey & Estreicher (Scheme 2 and 3). The structure of the bromonitro compound 9 was determined by an X-ray analysis, and the configurations of the bromonitro compounds 14, 18 and 22 were deduced from their molecular rotations. Reduction of the bromonitro compounds gave the protected 1-deoxy-l-nitroaldoses 2, 15/16, 19/20, and 24/25, respectively, in good overall yields. The ribose derivatives 15 and 16 were detritylated to give the nitro compound 4, and the mannose derivative 2 was partially deprotected to give the monoisopropylidene compound 26. The nitro group shows a normal anomeric effect which is reflected in the IR. spectra of the pyranose derivatives 19 and 20, and 24 and 25.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19820650302
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  • 3
    Electronic Resource
    Electronic Resource
    Deoxy-nitrosugars. 4th communication3rd Communication: [1].. Convenient synthesis of 1-deoxy-1-nitroaldoses (1983)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 66 (1983), S. 789-794 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new synthesis of 1-deoxy-1-nitroaldoses by ozonolysis of N-glycosylnitrones according to the procedure of Bailey et al. is described. Based on the oxime 1, the mannofuranosylnitrones 3-5 were obtained in yields of 86-88% and the 1-deoxy-1-nitromannose 6 in yields of 70-76%. In the same manner the 1-deoxy-1-nitroaldoses 9, 12, 18, and 19 were prepared in yields of 61-90% from the oximes 7, 10, 14 and 15, the procedure being compatible with the presence of free hydroxy groups.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19830660310
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  • 4
    Electronic Resource
    Electronic Resource
    L-Erythruronic Acid Derivatives as Building Blocks for Nucleoside Analogs. Synthesis of 4′-C-Aryl-D-ribonucleosides (1982)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 65 (1982), S. 2570-2582 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2, 3-O-Cyclohexylidene-L-erythruronic acid (6) available in 83% yield from D-ribonolactone (7), was treated with phenvlmagnesium bromide to give the D-ribo and L-lyxo derivatives 10 and 11 in high yields (Scheme 1 and 2). The diastereoselectivity depended on the temperature and mode of operation (Table 1). The absolute configuration of 10 and 11 was determined by correlation with (R)- and (S)phenylethanediol (17 and 16) respectively, excluding intramolecular hydride shifts during formation of 10 and 11. Reaction of 6 with methcoxymethoxyphenyllithium gave the lactones 18 and 19. The L-lyxo isomer 19 was transformed in high yields into the D-ribo lactone 18. Compound 10 was transformed into the adenosine analoge 24 by reduction with Diisobutylaluminium hydride, hydrolysis, acetylation and nucleoside synthesis according to Vorbrüggen (Scheme 3). Its structure was deduced from its UV., NMR. and CD. data and from those of the isopropylidene derivative 25. Similarly, 18 was transformed into the adenosine analog 29 and into the isopropylidene derivative 30.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19820650828
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  • 5
    Electronic Resource
    Electronic Resource
    Deoxy-nitrosugars. 6th communication5th Communication: [1].. Stereoelectronic control in the reductive denitration of tertiary nitro ethers. A synthesis of ‘C-glycosides’ (1983)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 66 (1983), S. 2210-2222 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The separate, radical denitration with Bu3SnH of the pyranose derivatives 3, 4, 9, and 10 gave in good yields exclusively the ‘C-glycosides’ 5 and 11, respectively (Scheme 1). Similar reduction of the cyclohexyl derivatives 15, 16, 19 and 20 gave 4:1 mixtures of 17, 18, 21 and 22, respectively, always with predominant formation of an axial C,H-bond. In the furanose series a divergent behaviour was observed for the D-mannose-derived nitro ethers 25 and 27 and the D-ribose-derived nitro ethers 30 and 31, respectively, in that the former two gave isomerically homogeneous reduction products (26 and 28, respectively; Scheme 3) and the latter a 1:1 mixture of the diastereoisomers 32 and 33 (Scheme 4). The stereochemical results were explained on the basis of the stereoelectronic effect of the ring O-atom, the preferred conformation of the intermediate, pyramidal alkoxyalkyl radicals and steric effects in the trioxabicyclo [3.3.0]octane ring system.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19830660733
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  • 6
    Electronic Resource
    Electronic Resource
    Synthesis of D- and L-5-Oxaproline and of a New Captopril Analogue (1983)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 66 (1983), S. 1241-1252 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 1,3-dipolar cycloaddition of the C-t-butyloxycarbonyl-N-mannosyl-nitrone 5, formed in situ from the partially protected D-mannose-oxime 3 and the glyoxylate 4, to ethylene gave preferentially the (3S)-N-glycosyl-isoxazolidine 6 which was transformed into the 3-isoxazolidine-carboxylate (L-5-oxaproline ester) 12 and into some derivatives thereof. The (S)-configuration of 12 was proved by chemical correlation with a derivative of L-asparagine. The D-5-oxaproline ester was obtained from the corresponding N-ribosyl-nitrone 24. Two protected dipeptides containing either C-terminal- (28) or N-terminal-5-oxaproline (= Opro) (30) were synthesized. Starting from 12, the analogue 1 of captopril® (2) was prepared and its activity as an inhibitor of the angiotensin-converting-enzyme (ACE) was examined.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19830660424
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  • 7
    Electronic Resource
    Electronic Resource
    Fragmentation of 6-Deoxy-6-halo-hexono-1,5-ortholactones: A Concerted, Nonstereospecific Process (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1328-1347 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the D-arabino- and D-ribo-ortholactones 13a-f and 15b-f and their treatment with Zn leading to the unsaturated esters 14a-d and 16a-d are described. Possible fragmentation mechanisms are discussed. The results were only compatible wit a concerted, nonsynchronous process, where both the axial lone pair of the ring oxygen atom and the lone pair formed during rupture of the C(5), O-bond participate in the elimination of the axial and of the equatorial C(1)-alkoxy groups, respectively.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670519
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  • 8
    Electronic Resource
    Electronic Resource
    Deoxy-nitrosugars 8th communication7th Communication: [1]. Convenient preparation of 1-C-nitroglycosyl chlorides. Halonitro ethers from hydroxy oximes (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1568-1571 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Partially protected 4- or 5-hydroxy-sugar oximes were transformed into 5- or 6-membered 1-C-nitroglycosyl chlorides, respectively, by reaction with NaOCl under phase-transfer conditions. With the exception of the oxidation of the gluco-derivative 1 giving the anomers 6 and 7, the reactions were completely diastereoselective.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670622
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  • 9
    Electronic Resource
    Electronic Resource
    Deoxy-nitrosugars, 7th communication6th Communication: [1]. Synthesis of methyl shikimate and of diethyl phosphashikimate from D-ribose (1984)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 67 (1984), S. 1562-1567 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The chain elongation of the deoxy-nitroribose 6 by a Michael addition to the vinyl-phosphonate 7 followed by a solvolysis gave the heptulosephosphonate 11 (87%). From 11, the key intermediates 15 and 16 (77%) were obtained by a highly diastereoselective reduction, followed by detritylation, periodate cleavage, and silylation. Methoxycarbonylation of 15 and 16 gave 17 and 18 which were converted into methyl shikimate (21; 79%) by intramolecular olefination and partial deprotection. Similarly, phosphonoylation of 16 gave 22 (99%) which was transformed into the diethyl phosphashikimate 2 (53% from 6).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19840670621
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  • 10
    Electronic Resource
    Electronic Resource
    Totalsynthese von Nojirimycin (1982)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 65 (1982), S. 1134-1144 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Total synthesis of NojirimycinAddition of the nitrone 3 (from 8 and 9) to furane, followed by oxidation with OsO4 and then isopropylidenation gave the fully functionalized glycoside 12 (40% from 8) via the glycal 10 and the hemiacetal 11. Since the glycoside cleavage of 12, leading to 13 after benzyloxycarbonylation proceeded in a mediocre yield, and since the acetolysis of 12 giving 14 (69%) was not practical, compound 12 was transformed into the hydroxy ester 17 by sequential hydrogenolysis, hydrolysis and benzyloxycarbonylation (69% overall). The hydroxy ester 17 was lactonized to give 18 (87%). Reduction of 18 first with LiBH4 (97%) and then with H2/Pd gave the key compound 20 which was transformed into nojirimycin (1) and into 1-deoxy-nojirimycin (2) using prior art. The overall yield of 1 was 19.5%.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19820650403
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