152343-98-1Relevant articles and documents
Enantiodivergent Formation of C-P Bonds: Synthesis of P-Chiral Phosphines and Methylphosphonate Oligonucleotides
Baran, Phil S.,Eastgate, Martin D.,Knouse, Kyle W.,Padial, Natalia M.,Rivas-Bascón, Nazaret,Schmidt, Michael A.,Vantourout, Julien C.,Xu, Dongmin,Zheng, Bin
, (2020)
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.
COMPOUNDS COMPOSITIONS AND METHODS INCLUDING THERMALLY LABILE MOIETIES
-
Page/Page column 113; 114, (2015/11/24)
The present invention generally relates to compounds that include one or more thermally labile protecting groups, compositions including the compounds, methods of making the compounds and compositions and methods of using the compounds and compositions. I
Efficient procedure for the synthesis of 3'-O-t-butyldimethylsilyl-2'-deoxynucleosides
Patil, Sucheta V.,Mane, Ramchandra B.,Salunkhe, Manikrao M.
, p. 1 - 2 (2007/10/02)
3'-O-t-Butyldimethylsilyl-2'-deoxynucleosides (3) have been synthesized in high yields by the reaction of 5'-O-DMT-2'-deoxynucleosides (1) with t-butyldimethylsilyl chloride (TBDMS-Cl) in THF using butyllithium followed by detritylation with 80percent aq.
