171775-22-7Relevant academic research and scientific papers
Enzymatic resolution of α-acetoxysulfides: A new approach to the synthesis of homochiral S,O-acetals
Milton,Brand,Jones,Rayner
, p. 1903 - 1906 (2007/10/03)
A novel enzymatic resolution of α-acetoxysulfides using Pseudomonas fluorescens lipase is reported. Selectivity is highly dependent on the substrate and solvent, with enantiomeric excesses of >95% in some cases. We believe these are the first examples of enzymatic resolutions of an S,O-acetal.
Enantioselective enzymatic synthesis of the anti-viral agent lamivudine (3TC)
Milton,Brand,Jones,Rayner
, p. 6961 - 6964 (2007/10/02)
A novel enzymatic resolution of α-acetoxysulfides has been used as the key step in the synthesis of the important antiviral nucleoside analogue lamivudine. The synthesis proceeds via a configurationally stable hemithioacetal which cyclises in situ to form the required oxathiolane nucleus, which can then be converted into the target nucleoside in 4 steps.
