Synthesis of 1,6-Anhydro-β-D-hexopyranoses Fused to the Piperidine Ring

[img]PDF - Authorized users only
Language: English
419Kb
Title:Synthesis of 1,6-Anhydro-β-D-hexopyranoses Fused to the Piperidine Ring
Creators:
Trtek, Tomáš
Černý, Miloslav
Buděšínský, Miloš
Trnka, Tomáš
Císařová, Ivana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 9, pp. 1429-1446
Uncontrolled Keywords:Cyclizations, Conformation analysis, X-Ray diffraction, Heterocycles, Oxiranes, 1,6-Anhydrosugars, Piperidines, Alkaloids, NMR spectroscopy, Carbohydrates

Abstract

Two piperidine derivatives (<strong>6</strong> and <strong>17</strong>) containing fused 1,6-anhydro-β-D-hexopyranose moiety were prepared from 1,6-anhydro-β-D-glucopyranose (<strong>1</strong>). The first synthetic route led via the known 1,6:2,3-dianhydro-4-deoxy-4-(3-hydroxypropyl)-β-D-mannopyranose (<strong>2</strong>) obtained in four steps from <strong>1</strong>. Its hydroxyl group was converted into amino group via tosylate and azide. The corresponding amino epoxide <strong>5</strong> readily rearranged into 3-amino-1,6-anhydro-3,4-dideoxy-3-<i>N</i>,4-<i>C</i>-(propane-1,3-diyl)-β-D-altropyranose (<strong>6</strong>). The second route used the known 1,6-anhydro-2,4-di-<i>O</i>-tosyl-β-D-<i>ribo</i>-hexopyranos-3-ulose (<strong>9</strong>) as an intermediate. Addition of allylmagnesium chloride to ketose <strong>9</strong> afforded 3-<i>C</i>-allyl-1,6-anhydro-2,4-di-<i>O</i>-tosyl-β-D-allopyranose (<strong>10</strong>). Hydroboration of its double bond followed by transformation of the resulting primary hydroxyl group into tosylamido group gave tritosyl derivative <strong>15</strong>. Intramolecular replacement of the tosyloxy group in position 4 by tosylamido group gave tosylated piperidine derivative <strong>16</strong>. Detosylation of <strong>16</strong> afforded the target 4-amino-1,6-anhydro-3,4-dideoxy-3-<i>C</i>,4-<i>N</i>-(propane-1,3-diyl)-β-D-gulopyranose (<strong>17</strong>). <p>

Title:Synthesis of 1,6-Anhydro-β-D-hexopyranoses Fused to the Piperidine Ring
Creators:
Trtek, Tomáš
Černý, Miloslav
Buděšínský, Miloš
Trnka, Tomáš
Císařová, Ivana
Uncontrolled Keywords:Cyclizations, Conformation analysis, X-Ray diffraction, Heterocycles, Oxiranes, 1,6-Anhydrosugars, Piperidines, Alkaloids, 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:9
Page Range:pp. 1429-1446
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20051429UNSPECIFIED
ID Code:2421
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) Synthesis of 1,6-Anhydro-β-D-hexopyranoses Fused to the Piperidine Ring. Collection of Czechoslovak Chemical Communications, 70 (9). pp. 1429-1446. ISSN 0010-0765

Repository Staff Only: item control page