133471-20-2

Basic information

• Product Name: (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>thymidine 3'-methylphosphonate
• CAS NO: 133471-20-2
• Molecular Weight: 1074.21
• Mol File: 133471-20-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>thymidine 3'-methylphosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>thymidine 3'-methylphosphonate(133471-20-2)
• EPA Substance Registry System: (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-deoxyadenoylyl-(3'->5')-N⁶-benzoyl-3'-O-<1,1-dimethylethyl)dimethylsilyl>thymidine 3'-methylphosphonate(133471-20-2)

Safety Data

• Hazardous Substances Data: 133471-20-2(Hazardous Substances Data)

Upstream product

• 40733-27-5 3'-O-(t-butyldimethylsilyl)thymidine 
• 40615-39-2 5'-O-(4-4'-dimethoxytrityl)thymidine 
• 80971-33-1 5'-O-(4,4'-dimethoxytrityl)-3'-O-(t-butyldimethylsilyl)-2'-deoxythymidine 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 118352-75-3 Triethylammonium 6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytrityl)adenosine 3'-H-phosphonate 
• 133471-14-4 (S_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 
• 74-88-4 methyl iodide 
• 133471-14-4 (R_P)-N⁶-benzoyl-5'-O-(4,4-dimethoxytrityl)-2'-adenoylyl-(3'->5')-3'-O-<1,1-dimethylethyl)dimethylsilyl>-thymidine 3'-H-phosphonate 

Downstream Products

• 71790-90-4 (R)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 71790-90-4 (S)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 90865-78-4 (S)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 
• 90865-77-3 (R)-Methyl-phosphonic acid (2R,3S,5R)-5-(6-benzoylamino-purin-9-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester (2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl ester 

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.