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Volumn 130, Issue 47, 2008, Pages 16031-16037

Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates using bicyclic oxazaphospholidine derivatives as monomer units

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; MOLECULAR ORBITALS; MONOMERS; PHOSPHORUS COMPOUNDS;

EID: 56749161695     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805780u     Document Type: Article
Times cited : (94)

References (65)
  • 37
    • 56749088959 scopus 로고    scopus 로고
    • 3 (1 equiv) were reacted in toluene in the presence of N-methylmorpholine (2 equiv) for 30 min at 0°C to room temperature. The mixture was filtered under argon to remove the resultant N-methylmorpholine hydrochloride and concentrated to dryness to afford crude 2a-d, which was used without further purification.
    • 3 (1 equiv) were reacted in toluene in the presence of N-methylmorpholine (2 equiv) for 30 min at 0°C to room temperature. The mixture was filtered under argon to remove the resultant N-methylmorpholine hydrochloride and concentrated to dryness to afford crude 2a-d, which was used without further purification.
  • 38
    • 56749166901 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 39
    • 0345097529 scopus 로고    scopus 로고
    • The oxazaphospholidine 6a was synthesized as a mixture of two isomers having either a (2S,4R,5R)- or a (2R,4S,5S)-oxazaphospholidine ring by using racemic 1,2-amino alcohol 7d. The 1,2-amino alcohols 7c,d were synthesized according to the procedures reported in the literature. The details are given in Supporting Information. (a) Bejjani, J.; Chemla, F.; Audouin, M. J. Org. Chem. 2003, 68, 9747-9752.
    • The oxazaphospholidine 6a was synthesized as a mixture of two isomers having either a (2S,4R,5R)- or a (2R,4S,5S)-oxazaphospholidine ring by using racemic 1,2-amino alcohol 7d. The 1,2-amino alcohols 7c,d were synthesized according to the procedures reported in the literature. The details are given in Supporting Information. (a) Bejjani, J.; Chemla, F.; Audouin, M. J. Org. Chem. 2003, 68, 9747-9752.
  • 41
    • 56749141846 scopus 로고    scopus 로고
    • The nucleoside 3′-O-oxazaphospholidine derivatives 5a-d were partially decomposed on silica gel during chromatography, resulting in modest isolated yields. The isolated 5a-d were stable for at least 1 year under proper storage conditions (at-30°C in a glass vial flushed with an inert gas).
    • The nucleoside 3′-O-oxazaphospholidine derivatives 5a-d were partially decomposed on silica gel during chromatography, resulting in modest isolated yields. The isolated 5a-d were stable for at least 1 year under proper storage conditions (at-30°C in a glass vial flushed with an inert gas).
  • 62
    • 0025302230 scopus 로고    scopus 로고
    • 3COIm as reported in the literature. (a) Heliński, J.; Skrzypczyński, Z.; Wasiak, J.; Michalski, J. Tetrahedron Lett. 1990, 31, 4081-4084.
    • 3COIm as reported in the literature. (a) Heliński, J.; Skrzypczyński, Z.; Wasiak, J.; Michalski, J. Tetrahedron Lett. 1990, 31, 4081-4084.
  • 65
    • 0001414996 scopus 로고    scopus 로고
    • Kong, J. et al. Spartan'04; Wavefunction, Inc.: Irvine, CA; J. Comput. Chem. 2000, 21, 1532-1548.
    • Kong, J. et al. Spartan'04; Wavefunction, Inc.: Irvine, CA; J. Comput. Chem. 2000, 21, 1532-1548.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.