Synthesis of 1-(3-Azido-2,3-dideoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pentofuranosyl)thymine and 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pent-2-enofuranosyl)thymine

[img]PDF - Authorized users only
Language: English
1112Kb
Title:Synthesis of 1-(3-Azido-2,3-dideoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pentofuranosyl)thymine and 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pent-2-enofuranosyl)thymine
Creators:
Hřebabecký, Hubert
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 2, pp. 409-420

Abstract

1-(2-<i>O</i>-Acetyl-3,5-di-<i>O</i>-benzoyl-4-<i>C</i>-benzoyloxymethyl-α-L-arabinofuranosyl)thymine (<i>II</i>) was converted to 2,2'-anhydro derivative <i>V</i> by selective deacetylation, mesylation and treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene. Cleavage of 2,2'-anhydro ring in compound <i>V</i> with hydrogen chloride or bromide afforded the respective 2'-chloro and 2'-bromo derivatives <i>VI</i> and <i>VII</i>. Reaction of compound <i>VII</i> with Cu/Zn couple and subsequent debenzoylation led to 1-(2,3-dideoxy-4-<i>C</i>-hydroxymethyl-α-L-pent-2-enofuranosyl)thymine (<i>IX</i>). Catalytic hydrogenation of <i>IX</i> gave 1-(2,3-dideoxy-4-<i>C</i>-hydroxymethyl-α-L-<i>glycero</i>-pentofuranosyl)thymine (<i>X</i>). Dehalogenation of compound <i>VI</i> with tributyltin hydride and debenzoylation afforded 1-(2-deoxy-4-<i>C</i>-hydroxymethyl-α-L-<i>erythro</i>-pentofuranosyl)thymine (<i>XII</i>). Tritylation of compound <i>XII</i>, followed by mesylation, detritylation and nucleophilic substitution with azide furnished 1-(3-azido-2,3-dideoxy-4-<i>C</i>-hydroxymethyl-α-L-<i>threo</i>-pentofuranosyl)thymine (<i>XXII</i>).

Title:Synthesis of 1-(3-Azido-2,3-dideoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pentofuranosyl)thymine and 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pent-2-enofuranosyl)thymine
Creators:
Hřebabecký, Hubert
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:2
Page Range:pp. 409-420
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19930409UNSPECIFIED
ID Code:165
Item Type:Article
Deposited On:06 Feb 2009 16:58
Last Modified:06 Feb 2009 15:58

Citation

Hřebabecký, Hubert; Holý, Antonín (1993) Synthesis of 1-(3-Azido-2,3-dideoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pentofuranosyl)thymine and 1-(2,3-Dideoxy-4-C-hydroxymethyl-α-L-glycero-pent-2-enofuranosyl)thymine. Collection of Czechoslovak Chemical Communications, 58 (2). pp. 409-420. ISSN 0010-0765

Repository Staff Only: item control page