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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Title: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
Creators:
Trtek, Tomáš
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
Císařová, Ivana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 69, 9, pp. 1818-1828
Uncontrolled Keywords:Cyclizations, X-Ray diffraction, Heterocycles, Amino sugars, 1,4-Oxazepanes, Epoxides, Oxiranes, 1,6-Anhydrosugars, NMR spectroscopy, Carbohydrates

Abstract

Some 1,4-oxazepanes based on 1,6-anhydro-β-D-hexopyranoses were prepared from 1,6:3,4-dianhydro-2-<i>O</i>-tosyl-β-D-galactopyranose (<strong>1</strong>). Cleavage of its oxirane ring with 3-chloropropanol gave 1,6-anhydro-4-<i>O</i>-(3-chloropropyl)-2-<i>O</i>-tosyl-β-D-glucopyranose (<strong>2</strong>), which was converted in three steps into 4-<i>O</i>-(3-aminopropyl)-1,6:2,3-dianhydro-β-D-mannopyranose (<strong>5</strong>). The latter compound underwent intramolecular cyclization to afford 3-amino-1,6-anhydro-3-deoxy-3-<i>N</i>,4-<i>O</i>-(propane-1,3-diyl)-β-D-altropyranose (<strong>6</strong>) that gave the corresponding quaternary ammonium salt <strong>10</strong> by <i>N</i>-methylation. Acid cleavage of the 1,6-anhydro bond in <strong>7</strong> gave&nbsp;the D-altrose derivative 3-acetamido-3-deoxy-3-<i>N</i>,4-<i>O</i>-(propane-1,3-diyl)-β-D-altropyranose (<strong>11</strong>). <p>

Title: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
Creators:
Trtek, Tomáš
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
Císařová, Ivana
Uncontrolled Keywords:Cyclizations, X-Ray diffraction, Heterocycles, Amino sugars, 1,4-Oxazepanes, Epoxides, Oxiranes, 1,6-Anhydrosugars, 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:69
Number:9
Page Range:pp. 1818-1828
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20041818UNSPECIFIED
ID Code:2307
Item Type:Article
Deposited On:06 Feb 2009 17:17
Last Modified:06 Feb 2009 16:17

Citation

Trtek, Tomáš; Černý, Miloslav; Trnka, Tomáš; Buděšínský, Miloš; Císařová, Ivana (2004) 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. Collection of Czechoslovak Chemical Communications, 69 (9). pp. 1818-1828. ISSN 0010-0765

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