66512-18-3

Upstream product

• 680-31-9 N,N,N,N,N,N-hexamethylphosphoric triamide 
• 50-89-5 thymidine 
• 1608-26-0 Hexamethylphosphorous triamide 
• 66386-45-6 thymidine nucleoside 3',5'-cyclic methyl phosphite 

Downstream Products

• 87970-10-3 5-Methyl-1-((2R,4aR,6R,7aS)-2-phenoxy-tetrahydro-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1H-pyrimidine-2,4-dione 
• 87970-09-0 cis-thymidine 3',5'-cyclic phenyl phosphite 
• 269403-65-8 thymidine cyclic 2-phenylallyl-3',5'-phosphite 
• 87970-09-0 cis-thymidine 3',5'-cyclic phenyl monophosphite 
• 143791-10-0 cis-thymidine 3',5'-cyclic p-nitrophenyl monophosphite 
• 108146-36-7 cis-phenyl ester of thymidine 3',5'-cyclic monophosphate 
• 108060-82-8 cis-thymidine 3',5'-cyclic o-nitrophenyl monophosphate 

Relevant academic research and scientific papers

Novel unique catalytic activating reagents in synthesis of biophosphates via the phosphoramidite route

Trimethylchlorosilane (TMSCI) and 2,4-dinitrophenol are remarkably efficient activators in reaction of P(III) amides with nucleosides to give P(III) esters in excellent yield.

Synthesis of nucleoside 3′,5′-cyclic boranophosphorothioate, a new type of cyclic nucleotide

The first examples of a borane-containing doubly P-modified chiral cyclic nucleoside monophosphate (cNMP), e.g., thymidine and 5-fluoro-2′-deoxyuridine 3′,5′-cyclic boranophosphorothioates, have been synthesized; these cNMP analogues with increased lipoph

Stereo- and Regiochemistries of the Oxidations of 2-Methoxy-5-tert-butyl-1,3,2-dioxaphosphorinanes and the Cyclic Methyl 3',5'-Phosphite of Thymidine by H2O/I2 and O2/AIBN to P-Chiral Phosphates. (17)O NMR Assignment of Phosphorus Configuration to the Diastereomeric Thymidine Cyclic ...

The stereo- and regiochemistries of oxidation of six-membered ring trialkyl phosphites under nonaqueous conditions with O2, initiated thermally or photochemically by azobis(isobutyronitrile) (AIBN), and with the well-known reagent H2O/I2 have been investigated.Yields of product phosphates are high, and both reactions occur regio- and stereospecifically with retention of configuration at phosphorus as shown for the diastereomeric 2-methoxy-5-tert-butyl-1,3,2-dioxaphosphorinanes and cyclic methyl 3',5'-phosphite triesters derived from thymidine.Mechanistic rationalesare proposed for both processes.These oxidations are useful for the facile introduction of (17)O or (18)O label into the phosphoryl oxygen of the product cyclic phosphate.Demethylation of the cyclic thymidine methyl 3',5'-monophosphate so-labeled yields the individual cyclic 3',5'-monophosphate diastereomers with (18)O or (17)O specifically axial or equatorial.The O2/AIBN oxidation can be proposed as a nonaqueous method for the oxidation of dinucleoside phosphite triesters and perhaps in the synthesis of oligonucleotides by the phosphite intermediate route as well. (17)O NMR is shown to be a convenient method to assign the absolute configuration at phosphorus to the individual oxygen-labeled diastereomers of the cyclic thymidine methyl 3',5'-monophosphate triester on the basis of their P=(17)O resonances, which are well-separated at 54.2 MHz (Δδ = 9.5, 515 Hz) and relatively narrow in CD3CN at 80 deg C.One-bond oxygen phosphorus couplings are well-resolved as well.Application of the (17)O results in the determination of the configurations of P-chiral thymidine 3'- and 5'-monophosphate diesters is proposed.

O2/AIBN, FREE-RADICAL METHOD FOR THE STEREOSPECIFIC OXIDATION OF NUCLEOSIDE TRIALKYL PHOSPHITES: NEW PREPARATION OF THE INDIVIDUAL, DIASTEREOMERIC, 18O-LABELED THYMIDINE 3',5'-CYCLIC MONOPHOSPHATES.

An experimentally easy method for regio- and stereospecific introduction of isotopic (18O or 17O) oxygen into phosphorus di- and triesters of biological interest is described and applied to 18O-labeling of cTMP's.