82101-87-9Relevant articles and documents
SmI2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: A highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate
Orsini, Fulvia,Caselli, Alessandro
, p. 7259 - 7261 (2007/10/03)
In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford β-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5′-(β-L-rhamnosyl)diphosphate.
Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates
Zurawinski, Remigiusz,Nakamura, Kaoru,Drabowicz, Jozef,Kielbasinski, Piotr,Mikolajczyk, Marian
, p. 3139 - 3145 (2007/10/03)
A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%.
REGIOCONTROLLED METALATION OF DIETYHL β-DIALKYLAMINOVINYLPHOSPHONATES: A NEW SYNTHESIS OF SUBSTITUTED β-KETOPHOSPHNATES
Boeckman, Robert K.,Walters, Michael A.,Koyano, Hiroshi
, p. 4787 - 4790 (2007/10/02)
The metalation of diethyl β-dialkylaminovinylphosphonates (vinylogous phosphoramides (VPA)) and their reaction with a variety of electrophiles is described.Upon mild hydrolysis these derivatives provide good yields of β-ketophosphonates.
