75715-12-7

Upstream product

• 195307-35-8 (Sp)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidylyl-(3'->5')-3'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-deoxythymidine 3'-methylphosphonate 
• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 80971-33-1 5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine 
• 108311-31-5 Methyl-phosphonic acid mono-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl] ester; compound with triethyl-amine 
• 108311-33-7 Carbonic acid (2R,3S,5R)-2-hydroxymethyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 83467-48-5 1-[(2R,4S,5R)-4-(tert-butyldiphenylsilanyloxy)-5-hydroxymethyltetrahydrofuran-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 108311-25-7 C₅₃H₆₅N₄O₁₅P 

Relevant academic research and scientific papers

Enantiodivergent Formation of C-P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides

Phosphorus Incorporation (PI, abbreviated Π) reagents for the modular, scalable, and stereospecific synthesis of chiral phosphines and methylphosphonate nucleotides are reported. Synthesized from trans-limonene oxide, this reagent class displays an unexpected reactivity profile and enables access to chemical space distinct from that of the Phosphorus-Sulfur Incorporation reagents previously disclosed. Here, the adaptable phosphorus(V) scaffold enables sequential addition of carbon nucleophiles to produce a variety of enantiopure C-P building blocks. Addition of three carbon nucleophiles to Π, followed by stereospecific reduction, affords useful P-chiral phosphines; introduction instead of a single methyl group reveals the first stereospecific synthesis of methylphosphonate oligonucleotide precursors. While both Π enantiomers are available, only one isomer is required - the order of nucleophile addition controls the absolute stereochemistry of the final product through a unique enantiodivergent design.

Methylphosphonate modified hairpin loops

We synthesized and analyzed DNA hairpin molecules with methylphosphonate linkages of defined stereochemistry in the loop region. Dinucleotide building blocks ApA and TpT (p indicating methylphosphonate linkage with either Rp or Sp configuration) were synt

SEPARATION OF DIASTEREOMERS OF METHYLPHOSPHONATE DINUCLEOTIDES

A chiral derivatizing agent, 1-menthyl chloroformate, has been used as a 3'-OH blocking group to facilitate the resolution of diastereomers of methylphosphonate dinucleotides by silica gel column chromatography.