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

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Title: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
Creators:
Trtek, Tomáš
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
Císařová, Ivana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 68, 7, pp. 1295-1308
Uncontrolled Keywords:Epoxides, Cyclizations, Oxiranes, 1,6-Anhydrosugars, Conformation analysis, Morpholines, X-Ray diffraction, Heterocycles, Amino sugars, Carbohydrates

Abstract

The key step of the synthetic route was opening of the oxirane ring in 1,6:3,4-dianhydro-2-<i>O</i>-tosyl-β-D-galactopyranose (<strong>1</strong>) with 2-chloroethanol to give 1,6-anhydro-4-<i>O</i>-(2-chloroethyl)-2-<i>O</i>-tosyl-β-D-glucopyranose (<strong>2</strong>), which was converted in four steps into 4-<i>O</i>-(2-aminoethyl)-1,6:2,3-dianhydro-β-D-mannopyranose (<strong>6</strong>). The latter compound underwent intramolecular cyclisation to afford the fused morpholine derivative 3-amino-1,6-anhydro-3-deoxy-3-<i>N</i>,4-<i>O</i>-ethylene-β-D-altropyranose (<strong>7</strong>) which gave the corresponding quaternary ammonium salt <strong>11</strong> by <i>N</i>-methylation. Acid cleavage of the 1,6-anhydro bond in <strong>7</strong> gave 3-acetamido-3-deoxy-3-<i>N</i>,4-<i>O</i>-ethylene-D-altropyranose (<strong>9</strong>). <p>

Title: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
Creators:
Trtek, Tomáš
Černý, Miloslav
Trnka, Tomáš
Buděšínský, Miloš
Císařová, Ivana
Uncontrolled Keywords:Epoxides, Cyclizations, Oxiranes, 1,6-Anhydrosugars, Conformation analysis, Morpholines, X-Ray diffraction, Heterocycles, Amino sugars, 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:68
Number:7
Page Range:pp. 1295-1308
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20031295UNSPECIFIED
ID Code:2120
Item Type:Article
Deposited On:06 Feb 2009 17:15
Last Modified:06 Feb 2009 16:15

Citation

Trtek, Tomáš; Černý, Miloslav; Trnka, Tomáš; Buděšínský, Miloš; Císařová, Ivana (2003) 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. Collection of Czechoslovak Chemical Communications, 68 (7). pp. 1295-1308. ISSN 0010-0765

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