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Volumn 6, Issue 5, 2004, Pages 839-841

N-(Phenylthio)-ε-caprolactam: A new promoter for the activation of thioglycosides

Author keywords

[No Author keywords available]

Indexed keywords

CAPROLACTAM DERIVATIVE; MESYLIC ACID DERIVATIVE; N (PHENYLTHIO) EPSILON CAPROLACTAM; OLIGOSACCHARIDE; THIOGLYCOSIDE; UNCLASSIFIED DRUG; LACTAM; N-(PHENYLTHIO)-EPSILON-CAPROLACTAM; SULFIDE;

EID: 1642357409     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0400084     Document Type: Article
Times cited : (84)

References (22)
  • 2
    • 84961328464 scopus 로고    scopus 로고
    • Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Weinheim
    • Oscarson, S. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 1, pp 93-116.
    • (2000) Carbohydrates in Chemistry and Biology , vol.1 , pp. 93-116
    • Oscarson, S.1
  • 12
    • 84985292620 scopus 로고
    • 1 is available from the Aldrich Chemical Co. (Rare Chemical Library); also, for the synthesis of 1, see: Sosnovsky, G.; Krogh, J. A. Synthesis 1979, 3, 228-230.
    • (1979) Synthesis , vol.3 , pp. 228-230
    • Sosnovsky, G.1    Krogh, J.A.2
  • 18
    • 1642268080 scopus 로고    scopus 로고
    • note
    • 2O, MeOTf) at the oxygen atom within amide bond-forming intermediate salts such as 4. However, we cannot rule out other possible pathways for activation such as S-triflation. Mechanistic studies are currently underway to elucidate the pathway of this reaction.
  • 19
    • 1642290741 scopus 로고    scopus 로고
    • note
    • 2O.
  • 20
    • 1642318515 scopus 로고    scopus 로고
    • note
    • 2O is an excellent promoter for low-temperature anomeric bond formation and remains our reagent of choice when attempting low-temperature glycosylations. 1 requires higher temperatures: typically, the reaction is initiated at -45°C and then allowed to warm to room temperature.
  • 22
    • 1642285835 scopus 로고    scopus 로고
    • note
    • 2O.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.