A convenient method for phosphorylation using triallyl phosphite

Recent advances in the chemical synthesis of sugar-nucleotides

“…The regent diallyl chlorophosphate is not commercially available and the authors also reported a convenient method for its synthesis and subsequently demonstrated the scope of their approach towards substituted mannose derivatives, D-Glc, D-Gal, L-Fuc and lactose. Soulère et al 24 have also recently shown that using a P III tri-O-allyl phosphite/I 2 system, in place of P V diallyl chlorophosphate, successfully synthesised β-1-phosphate derivatives of per-O-acyl D-Glc and D-Gal with comparable yields and selectivity.…”

Direct Aryloxylation/Alkyloxylation of Dialkyl Phosphonates for the Synthesis of Mixed Phosphonates

“…Then, the pyridine nucleophile attacks intermediate II to form the highly reactive electrophilic phosphorus species phosphoryl pyridin‐1‐ium ( III ) . Finally, intermediate III is transformed into the mixed phosphonate 3 a through a substitution reaction with phenol 2 a through TS2 ,…”

Efficient Synthesis of Phosphonamidates through One‐Pot Sequential Reactions of Phosphonites with Iodine and Amines

“…[11f] Therefore, to synthesize alkyl phosphonamidates by the present strategy, the reactionc onditions need to be further adjusted and explored. Based on the above resultsa nd the literature about the formation of iodophosphates from the Arbuzov reactiono ft rialkyl phosphite with iodine, [14] ap lausible mechanism was proposed in Scheme 4A.T he reactiono fi odine with aryl phosphonite would produce intermediate I,w hich could be attacked by iodide to form iodophosphonate II (Arbuzov reaction). Nucleophilic attack of iodophosphonate II by amines, with the elimination of HI, would lead to phosphonamidates 3.…”

“…The combination of phosphites and iodine is an established phosphorylationm ethod, which has been successfully applied to synthesize phosphoramidates and mixed phosphates. [14] Our group has extensively investigated this kind of iodine-mediated phosphoramidation reaction [15] and found it is av ery powerful and convenient way to access phosphoramidates. We reasoned that if we use phosphonites instead of phosphites in this reaction, phosphonamidates with one CÀPb ond would be produced.…”