New Heterocyclic Derivatives of 2-Amino-1,6-anhydro-2-deoxy-β-D-glucopyranose Containing 1,4-Oxazepane or Azepane Ring

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Title:New Heterocyclic Derivatives of 2-Amino-1,6-anhydro-2-deoxy-β-D-glucopyranose Containing 1,4-Oxazepane or Azepane Ring
Creators:
Trtek, Tomáš
Černý, Miloslav
Buděšínský, Miloš
Trnka, Tomáš
Císařová, Ivana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 4, pp. 466-478
Uncontrolled Keywords:Cyclizations, Conformation analysis, X-Ray diffraction, Heterocycles, Epoxides, 2-Amino-2-deoxy-D-glucose, Oxiranes, 1,6-Anhydrosugars, Azepanes, Oxazepanes, Aminosugars, NMR spectroscopy, Carbohydrates

Abstract

Two heterocyclic derivatives of D-glucosamine, 2-amino-1,6-anhydro-2-deoxy-2-<i>N</i>,4-<i>O</i>-(ethane1,2-diyl)-β-D-glucopyranose (<strong>13</strong>) and 2-amino-1,6-anhydro-2,4-dideoxy-2-<i>N</i>,4-(propane-1,3-diyl)-β-D-glucopyranose (<strong>14</strong>) were prepared from 1,6-anhydro-β-D-glucopyranose (levoglucosan) in ten steps via O-4 or C-4 substituted 1,6:2,3-dianhydro-β-D-mannopyranose derivatives <strong>2</strong> and <strong>4</strong>. Selective oxirane-ring cleavage with sodium azide at C-2 followed by tosylation afforded 2-azido-2-deoxy derivatives <strong>7</strong> and <strong>8</strong> of D-<i>gluco</i> configuration. These were reduced to amines and, after tosylation, azepane and oxazepane <i>N</i>-tosyl derivatives <strong>11</strong> and <strong>12</strong> were formed by intramolecular substitution. Their detosylation afforded the target D-glucosamine derivatives <strong>13</strong> and <strong>14</strong>. <p>

Title:New Heterocyclic Derivatives of 2-Amino-1,6-anhydro-2-deoxy-β-D-glucopyranose Containing 1,4-Oxazepane or Azepane Ring
Creators:
Trtek, Tomáš
Černý, Miloslav
Buděšínský, Miloš
Trnka, Tomáš
Císařová, Ivana
Uncontrolled Keywords:Cyclizations, Conformation analysis, X-Ray diffraction, Heterocycles, Epoxides, 2-Amino-2-deoxy-D-glucose, Oxiranes, 1,6-Anhydrosugars, Azepanes, Oxazepanes, Aminosugars, NMR spectroscopy, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:70
Number:4
Page Range:pp. 466-478
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20050466UNSPECIFIED
ID Code:2372
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Trtek, Tomáš; Černý, Miloslav; Buděšínský, Miloš; Trnka, Tomáš; Císařová, Ivana (2005) New Heterocyclic Derivatives of 2-Amino-1,6-anhydro-2-deoxy-β-D-glucopyranose Containing 1,4-Oxazepane or Azepane Ring. Collection of Czechoslovak Chemical Communications, 70 (4). pp. 466-478. ISSN 0010-0765

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