502494-87-3Relevant academic research and scientific papers
New mixed phosphonate esters by transesterification of pinacol phosphonates and their use in aldehyde and ketone coupling reactions with nonstabilized phosphonates
Reichwein, John F.,Pagenkopf, Brian L.
, p. 1459 - 1463 (2007/10/03)
Alkylpinacol phosphonates were prepared by rhodium-catalyzed olefin hydrophosphorylation, and attempted α-deprotonation of the pinacol derived alkyl phosphonates resulted in ring cleavage. The propensity of the alkylpinacol phosphonates to undergo ring opening was exploited to prepare phosphonic acid monomethyl esters in high yield by transesterification in acidulated methanol. Esterification and alkylation with aldehydes or ketones gave β-hydroxy mixed phosphonate esters. tert-Butyl and benzylic phosphonate ester protective groups were introduced to improve the efficiency and functional group compatibility of β-hydroxy phosphonate saponification. The β-hydroxy phosphonic acid monomethyl esters were dehydrated with diisopropylcarbodiimide, which gave oxaphosphetane intermediates that collapse to an olefin. The overall reaction sequence complements the arsenal of Horner-Wadsworth-Emmons-type coupling reactions.
Synthesis of C3 heteroatom-substituted azetidinones that display potent cholesterol absorption inhibitory activity
McKittrick, Brian A.,Ma, Ke,Huie, Keith,Yumibe, Nathan,Davis Jr., Harry,Clader, John W.,Czarniecki, Michael,McPhail, Andrew T.
, p. 752 - 759 (2007/10/03)
The C3 phenylpropyl side chain N-phenylazetidinones related to SCH 56524 was modified by replacing the hydroxymethylene with various isoelectronic or isosteric groups. Modifications at the 3' position led to less-active compounds; however, modifications a
