1026321-05-0Relevant articles and documents
Synthesis of carbocyclic pyrimidine nucleosides using the Mitsunobu reaction - Part I: Influence of the alcohol on N1- versus O2- alkylation
Ludek, Olaf R.,Meier, Chris
, p. 3145 - 3147 (2005)
The Mitsunobu reaction is an important tool in carbocyclic nucleoside chemistry for the direct coupling of alcohols with heterocyclic bases under mild conditions. Here, we report on the influence of the alcohol on the N1- vs. O2-alkylation of N
A linchpin carbacyclization approach for the synthesis of carbanucleosides
Leung, Leo M. H.,Gibson, Vicky,Linclau, Bruno
supporting information; experimental part, p. 9197 - 9206 (2009/04/06)
(Chemical Equation Presented) A convenient synthesis of carbanucleosides, with both enantiomers equally accessible, is reported. The key step is a tandem linchpin cyclization process to give access to substituted carbafuranose derivatives having the corre
Convergent or linear? A challenging question in carbocyclic nucleoside chemistry
Ludek, Olaf R.,Marquez, Victor E.
, p. 3451 - 3460 (2008/09/20)
North-methanocarbathymidine (N-MCT) is a carbocyclic nucleoside analogue with potent anti-HSV and KSHV activity. The critical step in the synthesis of N-MCT and other carbocyclic nucleoside analogues is the introduction of the nucleobase into the carbocyclic moiety. For this, convergent and linear strategies were compared side by side. In the convergent approach, the base was coupled to the carbocyclic moiety by either a Mitsunobu reaction or by displacement of a mesylate. This strategy leads to the formation of various amounts of the O2-regioisomer, depending on the applied procedure. Additionally, by-products of the Mitsunobu reaction have to be separated from the coupling products. Although lengthier, the linear strategy leads selectively to the target compound N-MCT with overall yields comparable to the convergent approaches, making this strategy more compatible for future large-scale syntheses. Georg Thieme Verlag Stuttgart.
