78186-91-1Relevant academic research and scientific papers
Determination of absolute configuration of the phosphonic acid moiety of fosfazinomycins
Schiessl, Katharina,Roller, Alexander,Hammerschmidt, Friedrich
, p. 7420 - 7426 (2013/10/22)
Fosfazinomycins A and B produced by Streptomyces lavendofoliae share the same phosphonate moiety with one chiral centre of unknown configuration which was determined by synthesising both enantiomers of 2-hydroxy-2-phosphonoacetic acid methyl ester. A chiral cyclic phosphite was reacted with methyl glyoxylate in a Pudovik reaction to give a pair of diastereomeric α- hydroxyphosphonates, which were separated by HPLC. The configurations at C-2 were assigned on the basis of single crystal X-ray structure analysis. Deprotection of these diastereomers furnished the enantiomeric α-hydroxyphosphonic acids, of which the (S)-configured had the same sign of optical rotation as the phosphonic acid moiety of the two fosfazinomycins.
Neighbouring Phosphonate Group Participation in Carbene Chemistry
Tomioka, Hideo,Hirai, Katsuyuki
, p. 1611 - 1613 (2007/10/02)
Systematic studies of the effect of the neighbouring phosphonate group on the reactivities of carbene showed that the neighbouring phosphonate group exerts prominent effects on both the product distribution and the reaction products; the results are interpreted as indicating the extent of participation, which seems to be sensitive to the carbenic substituents.
A CONVENIENT METHOD FOR THE SYNTHESIS OF Α-KETOESTERS FROM ALDEHYDES
Horne, David,Gaudino, John,Thompson, Wayne J.
, p. 3529 - 3532 (2007/10/02)
An efficient two step, two carbon homologation of aldehydes to α-ketoesters is described.
NEW ACYL ANION EQUIVALENT. A SHORT ROUTE TO THE ENOL LACTAM INTERMEDIATE IN CYTOCHALASIN SYNTHESIS
Nakamura, Eiichi
, p. 663 - 666 (2007/10/02)
The preparation and Emmons-Horner reactions of various α-alkoxyphosphonoacetates were examined.The latter reactions proceeded with considerable stereoselectivity, which allowed the efficient preparation of an intermediate in cytochalasin synthesis.
