Optically Active Furanoids Containing Cytosine-, Adenine- and Nicotinamide-Like Moieties

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Title:Optically Active Furanoids Containing Cytosine-, Adenine- and Nicotinamide-Like Moieties
Creators:
Werfeli, Ali
Voltrová, Svatava
Prutianov, Viktor
Kuthan, Josef
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 8, pp. 1223-1232
Uncontrolled Keywords:NADH model reduction, 5-Deoxy-β-D-ribofuranose derivatives

Abstract

3-Hydroxymethyl-5-(2,3-<i>O</i>-isopropylidene-β-D-<i>erythro-</i>furanosyl)-2-methylfuran (<strong>2</strong>) prepared from 3-ethoxycarbonyl derivative <strong>1 </strong>was converted to 3-chloromethyl-5-(2,3-<i>O</i>-isopropylidene-β-D-<i>erythro</i>-furanosyl)-2-methylfuran (<strong>3</strong>). Compound <strong>3</strong> reacted with cytosine, adenine, 6-chloropurine, 6-mercaptopurine, and nicotinamide to corresponding optically active heterocyclic derivatives <strong>5-10</strong> and <strong>14</strong>. The 6-chloro derivative <strong>9</strong> was converted to 6-alkoxy derivatives <strong>11</strong> and <strong>12</strong> by the reaction with methanol or ethanol, respectively, in the presence of diazabicyclooctane. Dithionite reduction of quaternary chloride <strong>14</strong> gave 1,4-dihydropyridine derivative <strong>15</strong> capable to transform ethyl phenylglyoxylate to optically active ethyl mandelate.

Title:Optically Active Furanoids Containing Cytosine-, Adenine- and Nicotinamide-Like Moieties
Creators:
Werfeli, Ali
Voltrová, Svatava
Prutianov, Viktor
Kuthan, Josef
Uncontrolled Keywords:NADH model reduction, 5-Deoxy-β-D-ribofuranose derivatives
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:8
Page Range:pp. 1223-1232
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19961223UNSPECIFIED
ID Code:1027
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:06

Citation

Werfeli, Ali; Voltrová, Svatava; Prutianov, Viktor; Kuthan, Josef (1996) Optically Active Furanoids Containing Cytosine-, Adenine- and Nicotinamide-Like Moieties. Collection of Czechoslovak Chemical Communications, 61 (8). pp. 1223-1232. ISSN 0010-0765

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