[5-(Adenin-9-yl)-5-deoxy-L-pentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. II. Synthesis of L-ribo and L-xylo Configurated Derivatives by Recyclization of Diethyl (5-RS)-[1,2-O-Isopropylidene-5-O-methanesulfonyl-D-pentofuranos-5-C-yl]phosphonates under Acidic Conditions

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Title:[5-(Adenin-9-yl)-5-deoxy-L-pentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. II. Synthesis of L-ribo and L-xylo Configurated Derivatives by Recyclization of Diethyl (5-RS)-[1,2-O-Isopropylidene-5-O-methanesulfonyl-D-pentofuranos-5-C-yl]phosphonates under Acidic Conditions
Creators:
Otmar, Miroslav
Rosenberg, Ivan
Masojídková, Milena
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 9, pp. 2180-2196

Abstract

Further cyclic analogs of the antiviral (<i>S</i>)-9-(3-hydroxy-2-phosphonomethoxypropyl)adenine (<i>I</i>) were prepared: both anomers of [5-(adenin-9-yl)-5-doxy-L-ribofuranosyl]phosphonic acid (α-<i>IId</i> and β-<i>IId</i>) and [5-(adenin-9-yl)-5-doxy-α-L-ribofuranosyl]phosphonic acid (<i>IIe</i>). Recyclization reaction of diethyl (5<i>RS</i>-(3-<i>O</i>-benzyl-1,2-<i>O</i>-isopropylidene-5-<i>O</i>-methanesulfonyl-D-ribofuranos-5-<i>C</i>-yl)phosphonate (<i>IVb</i>) and diethyl (5<i>RS</i>-(3-<i>O</i>-benzyl-1,2-<i>O</i>-isopropylidene-5-<i>O</i>-methanesulfonyl-D-xylofuranos-5-<i>C</i>-yl)phosphonate (<i>IVd</i>) in trifluoroacetic acid led to cyclic aldehydes <i>Va</i> and <i>Vb</i> which were reduced to diethyl α- and β-L-ribofuranosylphosphonates <i>VIb</i> and α-L-xylofuranosylphosphonate <i>VIIb</i>. Conversion to the protected 5-<i>O</i>-tosylates <i>VId</i> and <i>VIId</i>, followed by reaction with adenine and deprotection, afforded the mentioned nucleotide analogs <i>IId</i> and <i>IIe</i>. An attempt to prepare L-pentofuranosylphosphonates <i>Vc</i> and <i>XIII</i>, suitable for the synthesis of nucleotide analogs of 3-deoxy-L-<i>erythro</i> and L-<i>xylo</i> configuration (<i>IIf</i> and <i>IIg</i>, respectively) by the recyclization reaction of the corresponding 5-<i>O</i>-methanesulfonyl derivatives <i>IVf</i> and <i>XIIb</i> failed. In this case, anhydro derivatives <i>IXa, XVa</i> and <i>XVIa</i> were isolated and identified.

Title:[5-(Adenin-9-yl)-5-deoxy-L-pentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. II. Synthesis of L-ribo and L-xylo Configurated Derivatives by Recyclization of Diethyl (5-RS)-[1,2-O-Isopropylidene-5-O-methanesulfonyl-D-pentofuranos-5-C-yl]phosphonates under Acidic Conditions
Creators:
Otmar, Miroslav
Rosenberg, Ivan
Masojídková, Milena
Holý, Antonín
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:58
Number:9
Page Range:pp. 2180-2196
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19932180UNSPECIFIED
ID Code:337
Item Type:Article
Deposited On:06 Feb 2009 17:00
Last Modified:06 Feb 2009 16:00

Citation

Otmar, Miroslav; Rosenberg, Ivan; Masojídková, Milena; Holý, Antonín (1993) [5-(Adenin-9-yl)-5-deoxy-L-pentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. II. Synthesis of L-ribo and L-xylo Configurated Derivatives by Recyclization of Diethyl (5-RS)-[1,2-O-Isopropylidene-5-O-methanesulfonyl-D-pentofuranos-5-C-yl]phosphonates under Acidic Conditions. Collection of Czechoslovak Chemical Communications, 58 (9). pp. 2180-2196. ISSN 0010-0765

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