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Volumn 76, Issue 1, 2011, Pages 297-300

Practical synthesis of (2′ R)-2′-deoxy-2′-C-methyluridine by highly diastereoselective homogeneous hydrogenation

Author keywords

[No Author keywords available]

Indexed keywords

DIASTEREOSELECTIVE; DIASTEREOSELECTIVE HYDROGENATION; HOMOGENEOUS CONDITIONS; LOW LOADING; RH CATALYSTS; TITLE COMPOUNDS;

EID: 78650872293     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101822j     Document Type: Article
Times cited : (23)

References (24)
  • 3
    • 0003604405 scopus 로고    scopus 로고
    • 2 nd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY.
    • Gesteland, R. F.; Cech, T. R.; Atkins, J. F. The RNA World, 2 nd ed.; Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1999.
    • (1999) The RNA World
    • Gesteland, R.F.1    Cech, T.R.2    Atkins, J.F.3
  • 18
    • 78650915192 scopus 로고    scopus 로고
    • The yield for the two steps averaged 74% on a 10 kg scale. The reaction was inhibited by base, including imidazole, and promoted by water and AcOH. In spite of the thorough attempts to identify all variables in this reaction, on scale the reaction displayed a variable reaction time, and up to 48 h and addition of more reagent were employed in one case.
    • The yield for the two steps averaged 74% on a 10 kg scale. The reaction was inhibited by base, including imidazole, and promoted by water and AcOH. In spite of the thorough attempts to identify all variables in this reaction, on scale the reaction displayed a variable reaction time, and up to 48 h and addition of more reagent were employed in one case.
  • 19
    • 78650916711 scopus 로고    scopus 로고
    • note
    • 8.
  • 22
    • 78650909071 scopus 로고    scopus 로고
    • 1H NMR is quite sufficient to determine the level of silanol-related contaminants, given the high intensity of the isopropyl peaks.
    • 1H NMR is quite sufficient to determine the level of silanol-related contaminants, given the high intensity of the isopropyl peaks.
  • 23
    • 78650903461 scopus 로고    scopus 로고
    • In preliminary tests, hydrogenation of 6 was sluggish and less diastereoselective.
    • In preliminary tests, hydrogenation of 6 was sluggish and less diastereoselective.
  • 24
    • 78650866737 scopus 로고    scopus 로고
    • A full description of the screening results can be found in the Supporting Information.
    • A full description of the screening results can be found in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.