Stereoselective Synthesis of Phosphorothioate and Alkylphosphinate Analogs Using a l-Tryptophan Derived Chiral Auxiliary
β Scribed by Yixin Lu; George Just
- Publisher
- Elsevier Science
- Year
- 2000
- Tongue
- French
- Weight
- 204 KB
- Volume
- 56
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
AbstractΓA novel phosphorus containing ring system incorporating both imidazole and indole moieties has been synthesized and investigated. A new l-tryptophan derived chiral auxiliary which incorporates those elements has been prepared and used for the stereoselective synthesis of novel indolophosphorothioate and alkylphosphinate analogs.
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The use of phosphorothioates as DNA analogues useful in antisense-based therapy is well established and led to the development of Vitravene as the first antisense drug. Several other phosphorothioate oligonucleotides (PS-Oligos) are in clinical trials. Although Stec et al. described an elegant oxa
The use of phosphorothioates as DNA analogues useful in antisense-based therapy is well established [1] and led to the development of Vitravene as the first antisense drug. [2] Several other phosphorothioate oligonucleotides (PS-Oligos) are in clinical trials. Although Stec et al. described an elega
## Abstract For Abstract see ChemInform Abstract in Full Text.
1,2-Di-O-isopropylidene-3-C-cyanoethyl-5-deoxy-5-isopropylamino-D-xylofuranose 16a was synthesized. The use of 16a as a chiral auxiliary led to the diastereoselective formation of dithymidine phosphorothioate. The chiral auxiliary was easily removed by treatment with concentrated ammonia. 2-Mesityl-