Synthesis of 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pentofuranosyl)thymine and 1-(4-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)thymine

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Title:Synthesis of 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pentofuranosyl)thymine and 1-(4-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)thymine
Creators:
Hřebabecký, Hubert
Holý, Antonín
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 7, pp. 1668-1674

Abstract

Reaction of isopropylidene derivative <i>I</i> with thionyl chloride in hexamethylphosphoric triamide afforded chloro derivative <i>II</i>. Removal of the isopropylidene group in <i>II</i> by treatment with a cation-exchanging resin (H<sup>+</sup> form) gave the free chloro nucleoside <i>III</i>. reduction of the chloro derivative <i>II</i> with tributylstannane and subsequent removal of the isopropylidene group yielded deoxy derivative <i>V</i>. This was protected with tert-butyldiphenylsilyl group and converted into the mesylate <i>VII</i>. Elimination of the mesyl group followed by desilylation gave 1-(2,3-dideoxy-4-C-methyl-β-D-<i>glycero</i>-pent-2-enofuranosyl)thymine (<i>IX</i>) which was hydrogenated to afford 1-(2,3-dideoxy-4-C-methyl-β-D-<i>glycero</i>-pentofuranosyl)thymine (<i>X</i>). 1-(1-C-Azidomethyl-2-deoxy-β-D-<i>threo</i>-pentofuranosyl)thymine (<i>XIII</i>) was prepared by mesylation of the isopropylidene derivative <i>I</i>, nucleophilic substitution of the mesyl group with azide and removal of the isopropylidene group.

Title:Synthesis of 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pentofuranosyl)thymine and 1-(4-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)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:7
Page Range:pp. 1668-1674
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19931668UNSPECIFIED
ID Code:284
Item Type:Article
Deposited On:06 Feb 2009 16:59
Last Modified:06 Feb 2009 15:59

Citation

Hřebabecký, Hubert; Holý, Antonín (1993) Synthesis of 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pent-2-enofuranosyl)thymine, 1-(2,3-Dideoxy-4-C-methyl-β-D-glycero-pentofuranosyl)thymine and 1-(4-C-Azidomethyl-2-deoxy-β-D-threo-pentofuranosyl)thymine. Collection of Czechoslovak Chemical Communications, 58 (7). pp. 1668-1674. ISSN 0010-0765

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