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Volumn 33, Issue 7, 1994, Pages 709-722

Stereocontrolled Synthesis of Oligo(nucleoside phosphorothioate)s

Author keywords

Drug research; Medicinal chemistry; Nucleosides; Phosphorothioates

Indexed keywords


EID: 33748216395     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199407091     Document Type: Review
Times cited : (120)

References (218)
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    • J. Chem. Soc. Perkin Trans 1
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  • 163
    • 84989577651 scopus 로고    scopus 로고
    • The influence of DBU on configurational stability of P‐chiral organophosphates requires further study. Unpublished results from our laboratory (Z. J. Lesnikowski, L. Wozniak) indicate that diastereomers of dinucleoside 3′,5′‐methanephosphonates are not epimerized in the presence of DBU under conditions that lead to complete P‐epimerization of diastereomerically pure nucleoside 3′‐O‐(O‐4‐nitrophenylmethanephosphonate)s or nucleoside 3′‐O‐(Se‐methyl‐methanephosphonate)s. Therefore, these last results can be explained in terms of DBU‐catalyzed hydrolysis caused by traces of water; released p‐nitrophenoxide ion or methylselenenyl ion, respectively, may cause epimerization of parent compounds in the presence of DBU by a ping‐pong type mechanism.
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    • 12 34.4°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.