<i>tert</i>-Butyl Hypoiodate

Simpkins, Nigel S.; Wirth, Thomas

doi:10.1002/047084289x.rb389.pub2

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2014

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“…[39, 40] Such species are supposedly very moisture sensitive and should hydrolyze upon aqueous work-up. [41] …”

Section: Discussionmentioning

confidence: 99%

Iodine Monochloride Facilitated Deglycosylation, Anomerization, and Isomerization of 3-Substituted Thymidine Analogues

Khalil

Ishita

Ali

et al. 2014

Nucleosides, Nucleotides & Nucleic Acids

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The reaction of thymidine, 3-mono-, and 3,3′,5′-trialkylsubstitued thymidine analogues with iodine monochloride (ICl) was investigated. Treatment with ICl resulted in rapid deglycosylation, anomerization, and isomerization of thymidine and 3-substituted thymidine analogues under various reaction conditions leading to the formation of the nucleobases as the major products accompanied by minor formation of α-furanosidic-, α-pyranosidic- and β-pyranosidic nucleosides. On the other hand, 3,3′,5′-trisubstitued thymidine analogues were only deglycosylated and anomerized. These results are similar to those observed for the acidic hydrolysis of the glycoside bond in nucleosides, but were presumably caused by the Lewis acid character of an iodine electrophile.

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“…[39, 40] Such species are supposedly very moisture sensitive and should hydrolyze upon aqueous work-up. [41] …”

Section: Discussionmentioning

confidence: 99%