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Volumn 21, Issue 17, 2011, Pages 5050-5053

N-Methylimidazolium chloride-catalyzed pyrophosphate formation: Application to the synthesis of Lipid i and NDP-sugar donors

Author keywords

Lipid I; N Methylimidazolium chloride; NDP sugar donors; Phosphorimidazolide; Phosphoromorpholidate; Pyrophosphate formation

Indexed keywords

IMIDAZOLE DERIVATIVE; LIPID; N METHYLIMIDAZOLIUM CHLORIDE; NUCLEOPHILE; NUCLEOSIDE DIPHOSPHATE KINASE; PYROPHOSPHATE; SUGAR; UNCLASSIFIED DRUG;

EID: 80051783457     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.04.061     Document Type: Article
Times cited : (33)

References (50)
  • 35
    • 84857056491 scopus 로고    scopus 로고
    • 2 catalyst for Lipid IV synthesis in Ref. 3a, but its reproducibility turned out to be poor
    • 2 catalyst for Lipid IV synthesis in Ref. 3a, but its reproducibility turned out to be poor.
  • 38
    • 80051784549 scopus 로고    scopus 로고
    • Removal of MeOH and DMF from 7 and counter cation exchange of 8a, b with a trialkylamine are omitted in our method.
    • Removal of MeOH and DMF from 7 and counter cation exchange of 8a, b with a trialkylamine are omitted in our method.
  • 43
    • 0035840941 scopus 로고    scopus 로고
    • Wong's group reported that HBTU worked well for a condensation between protecting group-free UDP-MurNAc and protected pentapeptide:, However, in our case, HBTU and HATU afforded six-membered lactone and lactam at 4-OH and 2-NHAc along with the desired products, respectively
    • Wong's group reported that HBTU worked well for a condensation between protecting group-free UDP-MurNAc and protected pentapeptide: H. Liu, R. Sadamoto, P.S. Sears, and C.-H. Wong J. Am. Chem. Soc. 123 2001 9616 However, in our case, HBTU and HATU afforded six-membered lactone and lactam at 4-OH and 2-NHAc along with the desired products, respectively
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9616
    • Liu, H.1    Sadamoto, R.2    Sears, P.S.3    Wong, C.-H.4
  • 46
    • 0003189615 scopus 로고
    • This reaction proceeded faster in pyridine than DMF as reported in the following paper
    • This reaction proceeded faster in pyridine than DMF as reported in the following paper: J.G. Moffatt, and H.G. Khorana J. Am. Chem. Soc. 80 1958 3756
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 3756
    • Moffatt, J.G.1    Khorana, H.G.2
  • 47
    • 84857036539 scopus 로고    scopus 로고
    • In contrast to tetrazole catalyst, NMI·HCl promoted the reaction in pyridine as well as DMF.
    • In contrast to tetrazole catalyst, NMI·HCl promoted the reaction in pyridine as well as DMF.
  • 48
    • 84857042671 scopus 로고    scopus 로고
    • 7-DMF was observed in 30 min after addition of NMI·HCl (integral ratio of 7 to the new signal = ca. 5 to 1).
    • 7-DMF was observed in 30 min after addition of NMI·HCl (integral ratio of 7 to the new signal = ca. 5 to 1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.