211510-45-1

Upstream product

• 98-91-9 thiobenzoic acid 
• 927-74-2 3-Butyn-1-ol 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 

Downstream Products

• 647852-34-4 5-(4-benzoylthio-1-butynyl)-2'-deoxycytidine 
• 725735-79-5 5-(4-benzoylthiobut-1-ynyl)-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)uridine 
• 669776-71-0 5'-O-4,4'-dimethoxytrityl-5-(4-benzoylthio-1-butynyl)-2'-deoxycytidine 
• 647852-33-3 5-(4-benzoylthio-1-butynyl)-2'-deoxyuridine 

Relevant academic research and scientific papers

C-5 Modified nucleosides: Direct insertion of alkynyl-thio functionality in pyrimidines

A route is presented to append, in a single step, alkynyl thioesters to the 5-position of a pyrimidine ring of a nucleoside that is unprotected. These products should be useful to support in vitro selection experiments with functionalized DNA.

Attempts at vinyl radical carbonylation through cyclization onto carbonyl and cyano groups

Sulfanylvinyl radicals 4-6, 16, produced from toluenesulfanyl radical addition to alkynes 1-3, 15, gave only products arising from cyclization onto the thiophenyl ring and H-abstraction. No products were obtained deriving from possible 5-membered cyclization onto the esteric or thioesteric carbonyl group. Similar results were obtained from toluenesulfanyl radical addition to alkynyl nitriles 20 and 24, which did not provided any evidence for 5- or 6-membered vinyl radical cyclization onto the aliphatic cyano group. In contrast, both toluenesulfanyl- and benzenesulfanyl- vinyl radicals 32 and 37a smoothly cyclize onto the aromatic cyano group leading to ketones 35 and 39. This protocol represents a novel indirect radical carbonylation and provides a useful synthetic approach to indenones.