Intramolecular Cyclization of Some Acyclic Nucleoside Analogs

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Title:Intramolecular Cyclization of Some Acyclic Nucleoside Analogs
Creators:
Janeba, Zlatko
Holý, Antonín
Votavová, Hana
Masojídková, Milena
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 61, 3, pp. 442-457
Uncontrolled Keywords:Acyclic analogs, Purine derivatives, Nucleosides

Abstract

Reaction of stereoisomeric 8-bromo-9-(2,3-<i>O</i>-isopropylidene-2,3,4-trihydroxybutyl)adenines (<strong>8</strong>) with concentrated aqueous ammonia, sodium hydride, potassium <i>tert</i>-butoxide, or 1,8-diazabicyclo[5,4,0]undec-7-ene afforded 4e-<i>O</i>,8-anhydro-9-(2,3-<i>O</i>-isopropylidene-2,3,4-trihydroxybutyl)adenines <strong>9</strong> (derivatives of 1,3-oxazepino[2,3-<i>e</i>]adenine). The CD spectra of optically active stereoisomers of <strong>9</strong> have been studied and it was found that for <i>threo </i>isomers <strong>9a</strong> and <strong>9b</strong> their character corresponds to 5'-<i>O</i>,8-cycloadenosine. The compounds <strong>9</strong> were also prepared by oxidative cyclization of 9-(2,3-<i>O</i>-isopropylidene-2,3,4-trihydroxybutyl)adenines (<strong>7</strong>) with lead(IV) acetate in benzene. Reaction of 9-(4-hydroxybutyl)adenine (<strong>14</strong>) with lead(IV) acetate smoothly afforded the seven-membered ring derivative, 4'-<i>O</i>,8-anhydro-9-(4-hydroxybutyl)adenine (<strong>15</strong>); no anhydro products with five-, six-, and eight-membered ring were found. 2',3'-<i>O</i>-Isopropylideneinosine (<strong>16</strong>) reacted with lead(IV) acetate to give 5'-<i>O</i>,8-cyclo-2',3'-<i>O</i>-isopropylideneinosine (<strong>17</strong>) whereas 9-(4-hydroxybutyl)hypoxanthine (<strong>18</strong>) afforded no cyclic products.

Title:Intramolecular Cyclization of Some Acyclic Nucleoside Analogs
Creators:
Janeba, Zlatko
Holý, Antonín
Votavová, Hana
Masojídková, Milena
Uncontrolled Keywords:Acyclic analogs, Purine derivatives, Nucleosides
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:3
Page Range:pp. 442-457
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19960442UNSPECIFIED
ID Code:948
Item Type:Article
Deposited On:06 Feb 2009 17:05
Last Modified:06 Feb 2009 16:05

Citation

Janeba, Zlatko; Holý, Antonín; Votavová, Hana; Masojídková, Milena (1996) Intramolecular Cyclization of Some Acyclic Nucleoside Analogs. Collection of Czechoslovak Chemical Communications, 61 (3). pp. 442-457. ISSN 0010-0765

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