138310-65-3

Upstream product

• 27999-65-1 (3aS,4S,6R,6aR)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde 
• 362-43-6 2',3'-O-isopropylideneuridine 
• 138310-61-9 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil 

Downstream Products

• 1201555-80-7 1-[2,3-di-O-acetyl-5,6-dideoxy-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl]uracil 
• 138310-66-4 1-<5,6-dideoxy-6-(p-toluenesulfonyl)-β-D-erythro-hex-4(Z)-enofuranosyl>uracil 

Relevant academic research and scientific papers

Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues

Treatment of the protected (E)-5'-deoxy-5'-[(p-toluenesulfonyl)methylene] uridine and adenosine derivatives with tributyl- or triphenylgermane hydride (AIBN/toluene/) effected radical-mediated germyldesulfonylations to give 5'-(tributyl- or triphenylgermyl)methylene-5'-deoxyuridine and adenosine derivatives as single (E)-isomers. Analogous treatment of 2'-deoxy-2'- [(phenylsulfonyl)methylene]uridine with Ph3GeH afforded the corresponding vinyl triphenylgermane product. Stereoselective halodegermylation of the (E)-5'-(tributylgermyl)methylene-5'-deoxy nucleosides with N-iodosuccinimide or N-bromosuccinimide provided the Wittig-type (E)-5'-deoxy-5'-(halomethylene) nucleosides quantitatively, while no halodegermylations was observed with the 5'-deoxy-5'-(triphenylgermyl)methylene counterparts. Treatment of the vinyl trialkylgermanes with aqueous trifluoroacetic acid effected protiodegermylation, while vinyl triarylgermanes were stable under the acidic conditions.