A novel synthesis of α- and γ- fluoroalkylphosphonates

Abstract

a-Hydroxybenzylphosphonate esters are phosphonates undergo fluorination with allylic reefficiently converted into a-fluorobenzylphosphonate arrangement ; the corresponding phosphonic acids are esters by diethylaminosulphur trifluoride while the formed by de-esterification using bromo-or iodocorresponding a-hydroxyallyl-and cc-hydrosycinnamyl-trimethylsilane.

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

“…Due to the fact that enzyme binding may depend on the C-F stereochemistry, the synthesis of such compounds with a specific configuration is very important [9][10][11]. α-Fluorinated phosphonates can be prepared by many different protocols [12][13][14][15][16].…”

Boranophosphate Salts as an Excellent Mimic of Phosphate Salts: Preparation, Characterization, and Properties

“…The quest for phosphate bioisosters over the last several decades has included the synthesis of phosphonates, α-halo phosphonates, [32,33] phosphorothioates, [4] and boranophosphate analogues. [6,34,35] Despite the extensive study of boranophosphate nucleoside analogues, the exploration of the parent inorganic boranophosphate has not been reported.…”

Direct Screening for Phosphatase Activity by Turnover-Based Capture of Protein Catalysts This work was supported by BBSRC studentships (to J.B. and H.D.), by an EPSRC studentship (to J.H.R.), and by an EC TMR studentship (to S.C.-T.).

“…The thiol exchange moiety 2‐PySSCH 2 CH 2 NH 2 ( 9 ), prepared from bis‐2‐aminoethyldisulfide dihydrochloride in two steps,8 was coupled to 8 with EDC ( N ‐ethyl‐ N ′‐dimethylaminopropylcarbodiimide) to give disulfide ester 10 . Finally, selective cleavage of the phosphate ethyl esters of 10 with bromotrimethylsilane9 gave the suicide substrate 3 ( n =1) 10. Two higher homologues of 3 were synthesized by using glutaric anhydride and adipic anhydride, respectively 11…”