Synthesis of 5-Amino-5-deoxypentonolactams

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Title:Synthesis of 5-Amino-5-deoxypentonolactams
Creators:
Kefurt, Karel
Kefurtová, Zdeňka
Marková, Věra
Slívová, Karla
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 7, pp. 1027-1036
Uncontrolled Keywords:5-Amino-5-deoxypentonolactams, Synthesis, 5-Azido-5-deoxypentoses

Abstract

5-Azido-5-deoxy-1,2-<i>O</i>-isopropylidene-α-D-xylofuranose (<strong>4</strong>) and 5-azido-5-deoxy-1,2-<i>O</i>-isopropylidene-β-D-arabinofuranose (<strong>10</strong>) were prepared starting from D-xylose and D-arabinose, respectively. Using the oxidation-reduction way for the C-3 epimerization, 5-azido-5-deoxy-1,2-<i>O</i>-isopropylidene-α-D-ribofuranose (<strong>15</strong>) and 5-azido-5-deoxy-1,2-<i>O</i>-isopropylidene-β-D-lyxofuranose (<strong>17</strong>) were obtained from <strong>4</strong> and <strong>10</strong>, respectively. The derivatives <strong>4</strong>, <strong>10</strong>, <strong>15</strong> and <strong>17</strong> afforded by acid hydrolysis, oxidation with bromine and catalytic hydrogenation successively the corresponding 5-azido-5-deoxy-D-pentofuranoses <strong>6</strong>, <strong>11</strong>, <strong>18</strong>, <strong>19</strong>, 5-azido-5-deoxy-D-pentonolactones <strong>7</strong>, <strong>12</strong>, <strong>20</strong>, <strong>21</strong> and 5-amino-5-deoxy-D-pentonolactams <strong>8</strong>, <strong>13</strong>, <strong>22</strong>, <strong>23</strong>.

Title:Synthesis of 5-Amino-5-deoxypentonolactams
Creators:
Kefurt, Karel
Kefurtová, Zdeňka
Marková, Věra
Slívová, Karla
Uncontrolled Keywords:5-Amino-5-deoxypentonolactams, Synthesis, 5-Azido-5-deoxypentoses
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:61
Number:7
Page Range:pp. 1027-1036
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961027UNSPECIFIED
ID Code:1006
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Kefurt, Karel; Kefurtová, Zdeňka; Marková, Věra; Slívová, Karla (1996) Synthesis of 5-Amino-5-deoxypentonolactams. Collection of Czechoslovak Chemical Communications, 61 (7). pp. 1027-1036. ISSN 0010-0765

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