75715-12-7

Basic information

• Product Name: C₄₂H₄₇N₄O₁₃P
• Synonyms: C₄₂H₄₇N₄O₁₃P
• CAS NO: 75715-12-7
• Molecular Weight: 846.828
• Mol File: 75715-12-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₄₂H₄₇N₄O₁₃P(CAS DataBase Reference)
• NIST Chemistry Reference: C₄₂H₄₇N₄O₁₃P(75715-12-7)
• EPA Substance Registry System: C₄₂H₄₇N₄O₁₃P(75715-12-7)

Safety Data

• Hazardous Substances Data: 75715-12-7(Hazardous Substances Data)

Upstream product

• 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 
• 195307-35-8 (Sp)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxythymidylyl-(3'->5')-3'-O-[(1,1-dimethylethyl)diphenylsilyl]-2'-deoxythymidine 3'-methylphosphonate 
• 108311-25-7 C₅₃H₆₅N₄O₁₅P 

Relevant articles and documents

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.

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.