Collect. Czech. Chem. Commun. 1984, 49, 433-443
https://doi.org/10.1135/cccc19840433

Azido derivatives of 1,6-anhydro-β-D-hexopyranoses corresponding to 3-deoxy- and 4-deoxy-D-glucosamine

Ivan Černý, Tomáš Trnka and Miloslav Černý

Department of Organic Chemistry, Charles University, 128 40 Prague 2

Individual author index pages


Other CCCC articles of these authors

  • Pavel Vepřek, Kateřina Knytlová, Miroslav Ledvina, Tomáš Trnka and Jan Ježek
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  • Tomáš Trtek, Miloslav Černý, Miloš Buděšínský*, Tomáš Trnka and Ivana Císařová
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  • Tomáš Trtek, Miloslav Černý, Miloš Buděšínský*, Tomáš Trnka and Ivana Císařová
    New Heterocyclic Derivatives of 2-Amino-1,6-anhydro-2-deoxy-β-D-glucopyranose Containing 1,4-Oxazepane or Azepane Ring
    2005, Vol. 70, Issue 4, pp. 466–478 [Abstract]
  • Jan Veselý, Miroslav Ledvina*, Jindřich Jindřich, Tomáš Trnka and David Šaman
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  • Tomáš Trtek, Miloslav Černý, Tomáš Trnka, Miloš Buděšínský* and Ivana Císařová
    Synthesis of Some 1,4-Oxazepanes Fused with 1,6-Anhydro-β-D-hexopyranoses. 3,11,13-Trioxa-7-azatricyclo[8.2.1.02,8]tridecane Derivatives
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  • Ivan Černý, Helena Havlíková, Martin Hill, Richard Hampl and Vladimír Pouzar*
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  • Karel Zelenka, Tomáš Trnka, Iva Tišlerová, Vladimír Král, Mykhaylo Dukh and Pavel Drašar*
    Synthesis of Porphyrin Receptors Modified by Glycosylated Steroids
    2004, Vol. 69, Issue 5, pp. 1149–1160 [Abstract]
  • Tomáš Trtek*, Miloslav Černý, Tomáš Trnka, Miloš Buděšínský and Ivana Císařová
    Synthesis of Tricycles Based on 1,6-Anhydro-β-D-hexopyranoses Fused with Morpholine. 3,10,12-Trioxa-6-azatricyclo[7.2.1.02,7]dodecanes
    2003, Vol. 68, Issue 7, pp. 1295–1308 [Abstract]
  • Jan Veselý, Miroslav Ledvina*, Jindřich Jindřich, David Šaman and Tomáš Trnka
    Improved Synthesis of 1,2-trans-Acetates and 1,2-trans Ethyl 1-Thioglycosides Derived from 3,4,6-Tri-O-acetyl-2-deoxy-2-phthalimido-D-hexopyranosides
    2003, Vol. 68, Issue 7, pp. 1264–1274 [Abstract]
  • Jiří Kroutil*, Jindřich Karban, Tomáš Trnka, Miloš Buděšínský and Miloslav Černý
    Preparation of O-, S- and N-Benzyl Derivatives of 1,6-Anhydro-β-D-hexopyranoses via Aziridine Ring Opening
    2002, Vol. 67, Issue 12, pp. 1805–1819 [Abstract]
  • Miroslav Reschel, Miloš Buděšínský, Ivan Černý, Vladimír Pouzar and Pavel Drašar*
    Synthesis of Linear Steroid Oligoesters Based on Etienic Acid
    2002, Vol. 67, Issue 11, pp. 1709–1718 [Abstract]
  • Ivan Černý*, Miloš Buděšínský, Vladimír Pouzar and Pavel Drašar
    Linear Chaining of Etienic Acid Derivatives with the Amide Bond. Synthesis of Oligomeric Steroids
    2001, Vol. 66, Issue 6, pp. 933–946 [Abstract]
  • Jindřich Karban*, Miloš Buděšínský, Miloslav Černý and Tomáš Trnka
    Synthesis and NMR Spectra of 1,6-Anhydro-2,3-dideoxy-2,3-epimino- and 1,6-Anhydro-3,4-dideoxy-3,4-epimino-β-D-hexopyranoses
    2001, Vol. 66, Issue 5, pp. 799–819 [Abstract]
  • Petr Bartoš, Miloslav Černý*, Iva Tišlerová and Tomáš Trnka
    Synthesis of Unsaturated Sulfur-Linked (1→4)-Disaccharides by Substitution of Tosyloxy Group in 1,6-Anhydro-3,4-dideoxy-2-O-tosyl-β-D-erythro-hex-3-enopyranose with 1-Thiohexopyranoses
    2000, Vol. 65, Issue 11, pp. 1737–1744 [Abstract]
  • Ivan Černý*, Vladimír Pouzar, Miloš Buděšínský and Pavel Drašar
    Synthesis of Symmetrical Bis-Steroid Pyrazines Connected via D-Rings
    2000, Vol. 65, Issue 10, pp. 1597–1608 [Abstract]
  • Vladimír Pouzar*, Ivan Černý and Pavel Drašar
    Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Single-Protected α,ω-Diaminoalkanes
    1999, Vol. 64, Issue 12, pp. 2035–2043 [Abstract]
  • Vladimír Pouzar, Tereza Slavíková and Ivan Černý
    Lengthening of the Alkyl Chain in Steroid O-(ω-Carboxyalkyl)oximes by Wittig Reaction
    1998, Vol. 63, Issue 10, pp. 1623–1634 [Abstract]
  • Jiří Kroutil, Tomáš Trnka, Miloš Buděšínský and Miloslav Černý
    Preparation of 2,3-Dideoxy-2,3-epimino and 3,4-Dideoxy-3,4-epimino Derivatives of 1,6-Anhydro-β-D-hexopyranoses by Mitsunobu Reaction
    1998, Vol. 63, Issue 6, pp. 813–825 [Abstract]
  • Miroslav Ledvina, Daniel Zyka, Jan Ježek, Tomáš Trnka and David Šaman
    New Effective Synthesis of (N-Acetyl- and N-Stearoyl-2-amino-2-deoxy-β-D-glucopyranosyl)-(1→4)-N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine, Analogs of GMDP with Immunopotentiating Activity
    1998, Vol. 63, Issue 4, pp. 577–589 [Abstract]
  • Tereza Slavíková, Vladimír Pouzar and Ivan Černý
    Synthesis of Steroid O-(ω-Hydroxyalkyl)oximes by Reduction of Corresponding O-(ω-Carboxyalkyl)oxime Derivatives
    1998, Vol. 63, Issue 4, pp. 557–576 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Oldřich Lapčík and Richard Hampl
    Addition of Azoimide to Unsaturated Ketones in the Steroid Series. Synthesis of N-(17β-Hydroxy-3-oxo-5α-androstan-15β-yl)succinamoic Acid and Its Evaluation as Hapten for Dihydrotestosterone Immunoanalysis
    1997, Vol. 62, Issue 12, pp. 1931–1939 [Abstract]
  • Ivan Černý, Tereza Slavíková and Vladimír Pouzar
    Synthesis of (15E)-17β-hydroxy-5α-androstane-3,15-dione 15-[O-(Carboxymethyl)]oxime, New Hapten for Dihydrotestosterone (17β-hydroxy-5α-androstan-3-one)
    1997, Vol. 62, Issue 10, pp. 1642–1649 [Abstract]
  • Tereza Slavíková, Vladimír Pouzar and Ivan Černý
    Syntheses of Steroid O-(3-Carboxypropyl)oximes
    1997, Vol. 62, Issue 3, pp. 457–470 [Abstract]
  • Vladimír Pouzar, Tereza Slavíková and Ivan Černý
    Synthesis of (19E)-3β,7β-Dihydroxy-17-oxoandrost-5-en-19-al 19-(O-Carboxymethyl)oxime, New Hapten for 7β-Hydroxydehydroepiandrosterone (3β,7β-Dihydroxyandrost-5-en-17-one)
    1997, Vol. 62, Issue 1, pp. 109–123 [Abstract]
  • Jan Fajkoš, Vladimír Pouzar and Ivan Černý
    Synthesis of (15E)-3β-Hydroxyandrost-5-ene-15,17-dione 15-(O-Carboxymethyl)oxime; The New Hapten for 3β-Hydroxyandrost-5-en-17-one (Dehydroepiandrosterone, DHEA)
    1996, Vol. 61, Issue 11, pp. 1647–1654 [Abstract]
  • Miloslav Černý, Tomáš Trnka and Miloš Buděšínský
    Preparation and Reactions of 2-Chloroethyl 1-Thio-β-D-glycopyranosides Derived from D-Galactose, D-Glucose, and 2-Acetamido-2-deoxy-D-glucose
    1996, Vol. 61, Issue 10, pp. 1489–1500 [Abstract]
  • Vladimír Pouzar, Tereza Slavíková and Ivan Černý
    Preparation of 7-[O-(Carboxymethyl)oxime] Derivatives of Dehydroepiandrosterone and Pregnenolone
    1996, Vol. 61, Issue 3, pp. 404–412 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    Coupling of Steroid O-(Carboxymethyl)oxime Derivatives with Amino Alcohols
    1996, Vol. 61, Issue 2, pp. 288–297 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    Preparation of (20E)-21-Ethoxycarbonyl-14β,17α-pregna-5,20-dien-3β-yl Hydrogen Butanedioate
    1995, Vol. 60, Issue 4, pp. 715–718 [Abstract]
  • Miloš Buděšínský, Miloslav Černý, Ivan Černý, Stanislav Sámek and Tomáš Trnka
    Preparation of β-D-Glucopyranosyl Derivatives of 1,6:2,3- and 1,6:3,4-Dianhydro-β-D-hexopyranoses and Their 1H and 13C NMR Spectra
    1995, Vol. 60, Issue 2, pp. 311–323 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    17-(O-(2-Carboxyethyl)oxime) Derivatives of Androstanes of 3-Hydroxy-5α-, -5β-, -5-ene and 3-Oxo-4-ene Series
    1995, Vol. 60, Issue 1, pp. 137–149 [Abstract]
  • Ivan Černý, Miloš Buděšínský, Pavel Drašar and Vladimír Pouzar
    Construction of the Side-Chain in 14β-Androst-5-ene Derivatives. Preparation of 14β-Pregnenolone
    1994, Vol. 59, Issue 12, pp. 2691–2704 [Abstract]
  • Vladimír Pouzar and Ivan Černý
    Preparation of (17E)-3β-Hydroxyandrost-5-en-17-one (O-Carboxymethyl)oxime Derivatives with Short Peptide Chain
    1994, Vol. 59, Issue 9, pp. 2042–2056 [Abstract]
  • Vladimír Pouzar, Ivan Černý and Pavel Drašar
    Acrylate Side Chain Derivatives of 5β-Steroids
    1993, Vol. 58, Issue 12, pp. 2963–2976 [Abstract]
  • Libuše Arnoštová, Ivan Černý, Vladimír Pouzar and Pavel Drašar
    Synthesis of 5α-Cholestane Type Glycoside Sulfates
    1993, Vol. 58, Issue 5, pp. 1180–1190 [Abstract]
  • Vladimír Pouzar, Ivan Černý and Pavel Drašar
    Z-Isomers of Steroid 17β-Side Chain Methyl Acrylates
    1992, Vol. 57, Issue 9, pp. 1928–1936 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar and Miroslav Havel
    Glucosylation of Some Steroidal 17-Hydroxy Derivatives
    1992, Vol. 57, Issue 2, pp. 362–374 [Abstract]
  • Jindřich Jindřich, Miloslav Černý, Tomáš Trnka and Miloš Buděšínský
    The synthesis of 4-O-oligoethylene glycol derivatives of 1,6-anhydro-β-D-glucopyranose and crown-ethers formed by their intramolecular cyclization
    1991, Vol. 56, Issue 12, pp. 2950–2963 [Abstract]
  • Vladimír Pouzar, Hana Chodounská, Ivan Černý and Pavel Drašar
    Derivatives of 5α-androstan-3α- and 3β-ol with acrylonitrile side chain
    1991, Vol. 56, Issue 12, pp. 2906–2916 [Abstract]
  • Jiří Novotný, Jaroslav Podlaha and Miloslav Černý
    Crystal structure of 1,6-anhydro-1(6)-thio-β-D-glucopyranose S-oxide
    1991, Vol. 56, Issue 10, pp. 2169–2174 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Miloš Buděšínský, Pavel Drašar and Miroslav Havel
    Epimeric 17-hydroxy derivatives of 14β-androst-5-en-3β-yl acetate
    1990, Vol. 55, Issue 10, pp. 2510–2520 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    Preparation of (20E)-21-ethoxycarbonyl-5β-pregn-20-en-3β-yl hydrogen butanedioate
    1990, Vol. 55, Issue 6, pp. 1635–1638 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, George R. Pettit and Miroslav Havel
    Synthesis and in vitro antimetabolic evaluation of some steroidal thiazoles
    1989, Vol. 54, Issue 12, pp. 3339–3347 [Abstract]
  • Ivan Černý, Petr Novotný, Pavel Drašar, Miroslav Havel and Josef Pacák
    Glycosylation of steroids with silver silicate and 2-deoxy-2-fluoro-α-D-glucopyranosyl bromide triacetate
    1989, Vol. 54, Issue 10, pp. 2775–2783 [Abstract]
  • Marcela Krečmerová, Miloslav Černý, Miloš Buděšínský and Antonín Holý
    Utilization of 1,6-anhydrohexoses for the preparation of some aliphatic adenosine analogs
    1989, Vol. 54, Issue 10, pp. 2753–2766 [Abstract]
  • Stanislav Sámek, Tomáš Trnka and Miloslav Černý
    Reactivity of hydroxyl groups of 1,6 : 2,3- and 1,6 : 3,4-dianhydrido-β-D-hexapyranoses in methylation with iodomethane
    1988, Vol. 53, Issue 3, pp. 633–637 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar and Miroslav Havel
    β-Glucosides of steroidal unsaturated nitriles
    1987, Vol. 52, Issue 10, pp. 2521–2533 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    Preparation of (20E)-21-methoxycarbonyl-5,14,20-pregnatrien-3β-ol derivatives
    1987, Vol. 52, Issue 7, pp. 1803–1810 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar, Soňa Vašíčková and Miroslav Havel
    Preparation of 3β-hydroxy-21,26,27-trinorcholesta-5,23-dien-25→22-olide and 3β-hydroxy-20-(2-furyl)-21-nor-5-pregnene derivatives
    1987, Vol. 52, Issue 4, pp. 1043–1051 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    New approach to steroidal hemisuccinates and glycosides
    1987, Vol. 52, Issue 3, pp. 775–787 [Abstract]
  • Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    New method of preparation of cardioglycoside hemisuccinates
    1986, Vol. 51, Issue 9, pp. 2019–2028 [Abstract]
  • Stanislav Sekretár, Jan Kopecký and Miloslav Černý
    Photosensitized [2 + 2]-cycloaddition of 3-acetyl-2[3H]-oxazolone to maleic anhydride, dimethylmaleic anhydride, and 1,6-anhydro-4-O-benzyl-2,3-dideoxy-β-D-erythro-2-hexenopyranose
    1986, Vol. 51, Issue 4, pp. 899–902 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar, František Tureček and Miroslav Havel
    Steroids with the β-crotonate (2-butenoate) side chain
    1986, Vol. 51, Issue 1, pp. 128–140 [Abstract]
  • Soňa Vašíčková, Vladimír Pouzar, Ivan Černý, Pavel Drašar and Miroslav Havel
    Infrared spectra of compounds with the methoxymethyl protecting group
    1986, Vol. 51, Issue 1, pp. 90–100 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, Miroslav Havel, František Tureček, Daniela Schmiedová and Karel Vereš
    Preparation of 3-carboxypropanoates of digitoxin and digoxin and their conjugates with L-tyrosine
    1985, Vol. 50, Issue 12, pp. 2760–2774 [Abstract]
  • Tomáš Elbert and Miloslav Černý
    Reaction of 1,6-anhydro-4-O-benzyl-2-deoxy-2-isothiocyanato-β-D-glucopyranose; Preparation of 2-amino-1,6-anhydro-2,3-dideoxy-2,3-dideoxy-β-D-ribo-hexopyranose
    1985, Vol. 50, Issue 9, pp. 2000–2009 [Abstract]
  • Vladimír Pouzar, Pavel Drašar, Ivan Černý and Miroslav Havel
    Preparation and absolute configuration at C(22) of 21,26,27-trinor-5α-cholestan-25→22-olide derivatives
    1985, Vol. 50, Issue 4, pp. 869–877 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý and Miroslav Havel
    Synthesis of 4-(21-nor-5-pregnen-20-yl)-1,3-thiazole derivatives
    1984, Vol. 49, Issue 4, pp. 1051–1059 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, Jorga Smolíková and Miroslav Havel
    Synthesis of 17β-[4-(1,3-thiazolyl)]androstane 3β-hemisuccinate and glycoside
    1984, Vol. 49, Issue 4, pp. 1039–1050 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar, Miloš Buděšínský and Miroslav Havel
    Glucosylation of 5-androsten-3β-ol derivatives containing butenolide, furan or unsaturated ester moieties in the side chain
    1984, Vol. 49, Issue 4, pp. 881–891 [Abstract]
  • Vladimír Pouzar, Pavel Drašar, Ivan Černý and Miroslav Havel
    Preparation of 21,26,27-trinor-5α-cholest-23-en-25→20-olide from a propargyl synthone
    1984, Vol. 49, Issue 4, pp. 871–880 [Abstract]
  • Pavel Drašar, Ivan Černý, Vladimír Pouzar and Miroslav Havel
    New preparation of steroidal 3-hemisuccinates
    1984, Vol. 49, Issue 1, pp. 306–312 [Abstract]
  • Miloš Buděšínský, Miloslav Černý, Jitka Doležalová, Miloš Kulhánek, Josef Pacák and Milan Tadra
    4-Deoxy-4-fluoro-D-fructose: Preparation and structure
    1984, Vol. 49, Issue 1, pp. 267–274 [Abstract]
  • Miloslav Černý, Jitka Doležalová, Jindra Mácová, Josef Pacák, Tomáš Trnka and Miloš Buděšínský
    Preparation of 3-deoxy-3-fluoro-D-mannose and corresponding hexitol
    1983, Vol. 48, Issue 9, pp. 2693–2700 [Abstract]
  • Jan Schraml, Jaroslav Včelák, Miloslav Černý and Václav Chvalovský
    29Si NMR chemical shifts in pertrimethylsilylated 1,6-anhydro-β-D-glucopyranose derivatives. Empirical assignment from Hammett type dependence of the chemical shifts
    1983, Vol. 48, Issue 9, pp. 2503–2508 [Abstract]
  • Vladimír Pouzar, Soňa Vašíčková, Pavel Drašar, Ivan Černý and Miroslav Havel
    Preparation and absolute configuration at C(22) of 21,26,27-trinor-5α-cholestane-22,25-diol derivatives
    1983, Vol. 48, Issue 8, pp. 2423–2435 [Abstract]
  • Ivan Černý, Tomáš Trnka and Miloslav Černý
    Preparation of 2-amino-2,4-dideoxy-D-lyxo-hexopyranose (4-deoxy-D-mannosamine) from 1,6-anhydro-β-D-glucopyranose
    1983, Vol. 48, Issue 8, pp. 2386–2394 [Abstract]
  • Ivan Černý, Vladimír Pouzar, Pavel Drašar and Miroslav Havel
    Synthesis of 17β-steroidal 4-(2-butenolides)
    1983, Vol. 48, Issue 7, pp. 2064–2071 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý and Miroslav Havel
    Alternative syntheses of steroidal maleimides
    1983, Vol. 48, Issue 4, pp. 1224–1232 [Abstract]
  • Jitka Doležalová, Tomáš Trnka and Miloslav Černý
    Preparation of 1,6:3,4-dianhydro-β-D-altropyranose as starting substance for the synthesis of 3-substituted D-mannose derivatives
    1982, Vol. 47, Issue 9, pp. 2415–2422 [Abstract]
  • Pavel Drašar, Vladimír Pouzar, Ivan Černý, Miroslav Havel, Sofia N. Ananchenko and Igor V. Torgov
    Use of malonic acid derivatives for the construction of substituted side chains in the position 17β of steroids
    1982, Vol. 47, Issue 4, pp. 1240–1251 [Abstract]
  • František Tureček, Tomáš Trnka and Miloslav Černý
    Fragmentation of isomeric dideoxy derivatives of 1,6-anhydro-β-D-hexopyranoses under electron impact
    1981, Vol. 46, Issue 10, pp. 2390–2403 [Abstract]
  • Miloslav Černý, Hana Večerková, Ivan Černý and Josef Pacák
    Preparation of 2-amino-1,6-anhydro-2-deoxy-β-D-mannopyranose by intramolecular substitution of the tosyloxy group in sterically hindered position of 1,6-anhydro-2-O-p-tolylsulfonyl-β-D-glucopyranose
    1980, Vol. 45, Issue 6, pp. 1837–1844 [Abstract]
  • Miloš Buděšínský, Miloslav Černý, Tomáš Trnka and Soňa Vašíčková
    1H NMR spectra and the conformation of 1,6 : 2,3- and 1,6 : 3,4-dianhydro-β-D-hexopyranoses and their derivatives
    1979, Vol. 44, Issue 6, pp. 1965–1983 [Abstract]
  • Miloš Buděšínský, Tomáš Trnka and Miloslav Černý
    The 1H NMR spectra and the conformation of 1,6-anhydro-β-D-hexopyranoses and their triacetates
    1979, Vol. 44, Issue 6, pp. 1949–1964 [Abstract]
  • Josef Pacák, Zdislava Köllnerová and Miloslav Černý
    2-Deoxy-2-fluoro-D-glucosides. Preparation of 17-oxoestra-1,3,5(10)-trien-3-yl 2-deoxy-2-fluoro-β-D-glucopyranoside
    1979, Vol. 44, Issue 3, pp. 933–941 [Abstract]
  • Jaroslav Pecka and Miloslav Černý
    Stereoselective reduction of 1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) and of its 3,4-dihydro derivative with complex hydrides
    1978, Vol. 43, Issue 7, pp. 1720–1722 [Abstract]