“…Treatment of ( S) -prolinol with benzyl chloroformate, followed by O- mesylation and reaction with NaI, afforded iodide 13 (80%). A Michaelis−Becker reaction of 13 with the sodium salt of dimethyl phosphite gave phosphonate 14 (56%), and this intermediate was then hydrolyzed with 0.4 M NaOH at 90 °C to afford, after acidification, the desired phosphonic acid monomethyl ester 11 (60%). 1 …”
A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.
“…Treatment of ( S) -prolinol with benzyl chloroformate, followed by O- mesylation and reaction with NaI, afforded iodide 13 (80%). A Michaelis−Becker reaction of 13 with the sodium salt of dimethyl phosphite gave phosphonate 14 (56%), and this intermediate was then hydrolyzed with 0.4 M NaOH at 90 °C to afford, after acidification, the desired phosphonic acid monomethyl ester 11 (60%). 1 …”
A catalytic antibody-based approach toward the synthesis of an optically active pyrrolidine ring synthon potentially useful for ptilomycalin A is described. Enantiomerically pure hapten 37 was designed and constructed with the eventual goal of generating antibodies for the enantioselective partial hydrolysis of a meso diester such as 44 into a monoacid 45. This transition state analog possesses a phosphonate group containing the requisite oxyanionic character of the tetrahedral intermediate for ester hydrolysis. A newly developed carbamate-based linker, which was found to be much more hydrolytically stable than the commonly used glutarate ester, was developed for coupling of the hapten to a carrier protein.
Introduction
The Formation of
P
C
(
sp
3
) Bonds. Syntheses of Alkyl, Cycloalkyl and Aralkyl Phosphonic and Phosphinic Acids
The Formation of
P
C
(
sp
2
) Bonds. Syntheses of Alkenyl and Alkadienyl Phosphonic and Phosphinic Acids
The Formation of
P
C
(
sp
) Bonds. Syntheses of Alkynyl Phosphonic and Phosphinic Acids
The Formation of
P
C
(Aromatic) Bonds. Syntheses of Aryl Phosphonic and Phosphinic Acids
Syntheses of Phosphonic and Phosphinic Acids by Modification Procedures
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