1998
DOI: 10.1080/07328319808005183
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Stereocontrolled Synthesis of Dithymidine Phosphorothioates by Use of a Functionalized 5'- Protecting Group Bearing an Imidazole Residue

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Cited by 13 publications
(7 citation statements)
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“…The Hayakawa's attempt at the stereoselective synthesis based on using of tetrazole attached to a bulky chiral auxiliary resulted in only partial success, since in the best case the diastereoselection leading to corresponding phosphites was at the level of 65% [68]. Several other modifications of phosphoramidite method have been published but non of them allowed synthesis of constructs longer than dimers [69][70][71][72][73][74]. Also important results from Agrawal's works [75,76] on the synthesis of nearly-stereopure PS-oligos should be mentioned as well as successful stereocontrolled synthesis of long-mers reported from Beaucage's [77] and Hayakawa's [78] laboratories.…”
Section: Phosphorothioatesmentioning
confidence: 99%
“…The Hayakawa's attempt at the stereoselective synthesis based on using of tetrazole attached to a bulky chiral auxiliary resulted in only partial success, since in the best case the diastereoselection leading to corresponding phosphites was at the level of 65% [68]. Several other modifications of phosphoramidite method have been published but non of them allowed synthesis of constructs longer than dimers [69][70][71][72][73][74]. Also important results from Agrawal's works [75,76] on the synthesis of nearly-stereopure PS-oligos should be mentioned as well as successful stereocontrolled synthesis of long-mers reported from Beaucage's [77] and Hayakawa's [78] laboratories.…”
Section: Phosphorothioatesmentioning
confidence: 99%
“…Therefore approaches that replace this group are an attractive pathway toward improving stereoselectivity synthesis. Such strategies have involved the use of 2-trityl-4,5-dicyanoimidazole derivatives (Schell, Laux, & Engels, 1999), other trityl groups having an imidazolyl group (Wada, Kobayashi, Mori, & Sekine, 1998), and the addition of a linker to the phosphorus atom (Seio, Kumura, Bologna, & Sekine, 2003).…”
Section: Chirality Of Ps Oligonucleotidesmentioning
confidence: 99%
“…Various attempts at stereocontrolled synthesis of PS‐oligos undertaken by other research establishments have been reported, among them efforts directed towards stereospecific synthesis of dinucleoside 3′,5′‐phosphorothioates (Jin et al, ; Jin and Just, ; Wada et al, ; Wang and Just, ; Lu and Just, ; Oka et al, ), Agrawal's work on the synthesis of nearly stereopure PS‐oligos (Iyer et al, ), and the successful stereocontrolled synthesis of long‐mers reported by Beaucage's laboratory (Wilk et al, ). These groups utilized the ingenious phosphoramidite methodology originally developed by Beaucage and Caruthers ().…”
Section: Commentarymentioning
confidence: 99%