Synthesis of Carba Analogues of Deoxy-4-C-(hydroxymethyl)hexopyranoses, Intermediates in the Synthesis of Carbocyclic Nucleosides

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Title:Synthesis of Carba Analogues of Deoxy-4-C-(hydroxymethyl)hexopyranoses, Intermediates in the Synthesis of Carbocyclic Nucleosides
Creators:
Hřebabecký, Hubert
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 66, 5, pp. 785-798
Uncontrolled Keywords:Carbocyclic hexopyranoses, Carbasugars, Glucose, Substituted 1,1-bis(hydroxymethyl)cyclohexanes, Pseudosugars, Cyclitols, Cyclohexanes, Carbohydrates

Abstract

3-<i>O</i>-Benzyl-1,2-<i>O</i>-isopropylidene-α-D-glucofuranose-5,6-<i>O</i>-sulfate (<strong>1</strong>) was treated with sodium salt of dimethyl malonate to obtain, after hydrolysis, methyl 5-(3-<i>O</i>-benzyl-1,2-<i>O</i>-isopropylidene-α-D-erythrofuranos-4-yl)-2-oxotetrahydrofuran-3-carboxylate (<strong>3</strong>) which was converted to the mixture of methyl (2<i>S</i>,3<i>R</i>,4<i>R</i>)- (<strong>7</strong>) and (2<i>R</i>,3<i>R</i>,4<i>R</i>)-2-(acetyloxy)-3-(benzyloxy)-4-(formyloxy)-7-oxo-6-oxabicyclo[3.2.1]octane-1-carboxylate (<strong>8</strong>). The compound <strong>7</strong> was reduced with lithium aluminium hydride to give (1<i>R</i>,2<i>R</i>,3<i>R</i>,4<i>S</i>)-3-(benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol (<strong>9</strong>) which was transformed to (1<i>R</i>,2<i>S</i>,4<i>R</i>)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol (<strong>14</strong>). Treatment of sodium salt of diethyl malonate with 3-<i>O</i>-benzyl-5,6-dideoxy-6-iodo-1,2-<i>O</i>-isopropylidene-α-D-<i>xylo</i>-hexofuranose (<strong>19</strong>) gave diethyl (3-<i>O</i>-benzyl-5,6-dideoxy-1,2-<i>O</i>-isopropylidene-α-D-<i>xylo</i>-hexofuranos-6-yl)malonate (<strong>20</strong>) which was converted to (1<i>R</i>,3<i>R</i>)-4,4-bis(hydroxymethyl)cyclohexane-1,3-diol (<strong>28</strong>) by a similar procedure to that used for <strong>14</strong>. <p>

Title:Synthesis of Carba Analogues of Deoxy-4-C-(hydroxymethyl)hexopyranoses, Intermediates in the Synthesis of Carbocyclic Nucleosides
Creators:
Hřebabecký, Hubert
Holý, Antonín
Uncontrolled Keywords:Carbocyclic hexopyranoses, Carbasugars, Glucose, Substituted 1,1-bis(hydroxymethyl)cyclohexanes, Pseudosugars, Cyclitols, Cyclohexanes, 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:66
Number:5
Page Range:pp. 785-798
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20010785UNSPECIFIED
ID Code:1823
Item Type:Article
Deposited On:06 Feb 2009 17:13
Last Modified:06 Feb 2009 16:13

Citation

Hřebabecký, Hubert; Holý, Antonín (2001) Synthesis of Carba Analogues of Deoxy-4-C-(hydroxymethyl)hexopyranoses, Intermediates in the Synthesis of Carbocyclic Nucleosides. Collection of Czechoslovak Chemical Communications, 66 (5). pp. 785-798. ISSN 0010-0765

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