74124-44-0

Upstream product

• 868-85-9 Dimethyl phosphite 
• 100-46-9 benzylamine 
• 67-56-1 methanol 
• 33985-75-0 phosphoramidic acid, N-(phenylmethyl)-, diphenyl ester 
• 96-36-6 methyl phosphite 
• 26773-69-3 N-(phenylmethyl)-2-benzothiazolesulfenamide 
• 100-44-7 benzyl chloride 
• 622-79-7 benzyl azide 
• 121-45-9 phosphorous acid trimethyl ester 
• 100-39-0 benzyl bromide 
• 130012-35-0 dimethyl N-benzylphosphoramidothionate 

Relevant academic research and scientific papers

Two scaffolds from two flips: (α,β)/(β,γ) CH2/NH "met-Im" analogues of dTTP

Novel α,β-CH2 and β,γ-NH (1a) or α,β-NH and β,γ-CH2 (1b) "Met-Im" dTTPs were synthesized via monodemethylation of triethyl-dimethyl phosphorimido-bisphosphonate synthons (4a, 4b), formed via a base-induced [1,3]-rearrangement of precursors (3a, 3b) in a reaction with dimethyl or diethyl phosphochloridate. Anomerization during final bromotrimethylsilane (BTMS) deprotection after Mitsunobu conjugation with dT was avoided by microwave conditions. 1a was 9-fold more potent in inhibiting DNA polymerase β, attributed to an NH-group interaction with R183 in the active site.

An efficient synthesis of phosphoramidates from halides in aqueous ethanol

An environment friendly and efficient synthesis of primary phosphoramidates has been developed from benzyl/allyl/alkyl/propargyl halides in aqueous ethanol as a green reaction medium via in-situ formation of azide. The method is simple, metal free and high yielding at room temperature with wide substrate scope and functional group compatibility. The optimized protocol can be used for synthesis of phosphoramidate intermediates used as prodrug moieties to improve therapeutic potential of the parent drug.

Phosphoramidate synthesis via copper-catalysed aerobic oxidative coupling of amines and H-phosphonates

The copper-catalysed oxidative coupling of amines and H-phosphonates to produce phosphoramidates has been achieved using CuI as the catalyst and O 2 (present in air) as the sole oxidant.

Stereoselective and chemoselective oxidation of phosphorothionates using MMPP

MMPP (monoperoxyphthalic acid, magnesium salt) converts phosphorothionates to the corresponding oxons in good yields with excellent chemoselectivity and stereoselectivity.

Umsetzung von 2-Azidoalkoholen mit Trialkylphosphiten. Bildung von Aziridinen und Amidophosphorsaeureestern via Imidophosphorsaeureester und 1,3,2λ5-Oxazaphospholidine

The 2-azidoalcohols 1 and 2 react with trialkyl phosphites to trialkyl (2-hydroxyalkyl)imidophosphates 10, 14, and 15 respectively, whereas the 2-azidoalcohols 3-7 yield the 2,2,2-trialkoxy-1,3,2λ5-oxazaphospholidines 16-22 under the same reaction conditions (Scheme 2).The dialkyl (2-hydroxyalkyl)amidophosphates 23, 25, and 27-34 are obtained by the reaction of 10, and 14-22 with water (Scheme 3 and 4).By reaction with alcohols, however, both the imidophosphates 10, 14, and 15 and the 1,3,2λ5-oxazaphospholidines 16-22 are transformed to aziridines 24, 26, and 35-38 (S cheme 5).The reactions of the imidophosphates seem to proceed via 1,3,2λ5-oxazaphospholidines.

REACTION OF SULFENAMIDES WITH DI-ALKYL AND TRIALKYL PHOSPHITES. AN EFFICIENT SYNTHESIS OF PHOSPHORAMIDATES BY UNUSUAL SUBSTITUTION AT S-N BOND IN (2-BENZOTHIAZOLYL)SULFENAMIDES

Regioselective attack of the trivalent phosphorus atom of dialkyl and trialkyl phosphites on either nitrogen or sulfur atom of sulfenamides has been found.The reaction of phenylsulfenamides with dialkyl phosphites yielded phosphorothiolates, whereas the treatment of (2-benzothiazolyl)sulfenamides with dialkyl and trialkyl phosphites gave phosphoramidates in excellent yields.

SOLVOLYSIS OF DIPHENYL AMIDOPHOSPHATES IN AQUEOUS ALCOHOLIC MEDIA

Influence of substituent on the reaction rate of the alkali-catalyzed solvolysis of the studied compounds set has been followed.The activation entropy has also been determined.The reaction products have been identified, and their concentration ratio has been determined.The reaction selectivity is mostly influenced by sterical effects in the substrate molecule.The results obtained agree with the SN2 mechanism.

Electrosynthesis of heteroatom bonds. 5. Direct cross-coupling of dialkylphosphites with amines by an iodonium ion-promoted electrolytic procedure

An efficient direct cross-coupling procedure of dialkylphosphites with amines by an iodonium ion-promoted electrolysis, givin N-substituted dialkyl phosphoramidates, has been proposed.