2,2'-Anhydro-4'-thionucleosides: Precursors for 2'-azido- and 2'-chloro-4'-thionucleosides and for a novel thiolane to thietane rearrangement

Article abstract of DOI:10.1080/15257770008033855

2,2'-Anhydro-4'-thio-β- and α-nucleosides 9 and 10 have been prepared by an in situ 4-thio-1,2-glycal addition route. They undergo ring-opening by azide or chloride ion to give, after deprotection, the 2'-substituted-4'-thionucleosides 13 and 14, whereas reactions with cyanide or fluoride sources lead to the unsaturated nucleosides 17 or 15, depending upon conditions. An unexpected and clean rearrangement to the thietane 23 occurs on treatment of uracil derivative 20 with DAST.

Full text of DOI:10.1080/15257770008033855

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2,2′-Anhydro-4′-Thionucleosides:
Precursors for 2′-Azido- and 2′-
Chloro-4′-thionucleosides and
for a Novel Thiolane to Thietane
Rearrangement
J. Allen Miller a , Ashley W. Pugh a & G. Mustafa Ullah a
a Department of Medicinal Chemistry, Wellcome Research
Laboratories, Beckenham, Kent, BR3 3BS, U.K.
Published online: 24 Sep 2006.
To cite this article: J. Allen Miller , Ashley W. Pugh & G. Mustafa Ullah (2000): 2,2′-Anhydro-4′-
Thionucleosides: Precursors for 2′-Azido- and 2′-Chloro-4′-thionucleosides and for a Novel Thiolane to
Thietane Rearrangement, Nucleosides, Nucleotides and Nucleic Acids, 19:9, 1475-1486
To link to this article: http://dx.doi.org/10.1080/15257770008033855
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