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Volumn 64, Issue 22, 1999, Pages 8090-8097

Indolyl-oxazaphosphorine precursors for stereoselective synthesis of phosphite triesters and dithymidinyl phosphorothioates

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHITE; PHOSPHOROTHIOIC ACID DERIVATIVE;

EID: 0033615709     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990242l     Document Type: Article
Times cited : (21)

References (26)
  • 21
    • 0344161321 scopus 로고    scopus 로고
    • note
    • We thank Dr. S. L. Beaucage for proposing an epimerization mechanism. (equation presented)
  • 22
    • 0345023956 scopus 로고    scopus 로고
    • note
    • The synthesis of diol (R)-and (S)-14 was scaled up by Dalton Chemical Laboratories, Inc., Ontario, Canada. The chiral auxiliaries 5c and 5d were synthesized in (S) configuration because of the avaiable of starting material (S)-14.
  • 23
    • 0344592917 scopus 로고    scopus 로고
    • note
    • Although nitrile 5b (96% ee) was used, only two diastereomers of indolyl-oxazaphosphorine 7b were observed. Probably because of the limitation of detection, the minor compounds could not be detected.
  • 24
    • 0344161320 scopus 로고    scopus 로고
    • note
    • A mixture of dry dichloromethane and acetonitrile (1:10) was used as eluting solvent. Using ethyl acetate instead of acetonitrile gave very low yield of 7b. The trace of acids in ethyl acetate probably accelerated the decomposition of 7b.
  • 25
    • 0345023954 scopus 로고    scopus 로고
    • note
    • The snake venom phosphodiesterase and P1 nuclease digestion and HPLC analysis were carried out at ISIS Pharmaceuticals (Carlsbad, CA) by Dr. M. Manoharan.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.