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Volumn 7, Issue 12, 2005, Pages 2361-2364

A tuneable method for N-debenzylation of benzylamino alcohols

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINO ACID DERIVATIVE; BENZENE DERIVATIVE; CARBOHYDRATE DERIVATIVE; IODINE DERIVATIVE;

EID: 20544457347     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050624f     Document Type: Article
Times cited : (29)

References (31)
  • 23
    • 20544450473 scopus 로고    scopus 로고
    • note
    • Interestingly, treatment of 7 with 5 equiv of NIS, followed by 1 equiv of water (2 h when TLC indicated no 7) gave 9 in improved 87% yield (entry 21).
  • 25
    • 20544478329 scopus 로고    scopus 로고
    • note
    • Low nucleophilicity acceptors gave 47-49% glycosylsuccinimide.
  • 26
    • 20544478558 scopus 로고    scopus 로고
    • note
    • Lower yield of 31 may be from volatility.
  • 27
    • 20544453986 scopus 로고    scopus 로고
    • note
    • Three equivalents of NIS gave 60% 24 with 20% monodebenzylated- monobenzoylated 18. O-Benzyldecyl ether did not debenzylate with 3 equiv of NIS, and control of NIS (2 equiv) gave more 24 from 23.
  • 28
    • 20544472269 scopus 로고    scopus 로고
    • note
    • Products detected by TLC not necessarily present in the reaction mixture and may be the result of hydrolysis of intermediates.
  • 29
    • 20544446563 scopus 로고    scopus 로고
    • Landoh-Bornstein, A.: Fischer, H., Hellwege, I.-H.,Springer-Verlag: Berlin, 1985; Vol. 9, Part d
    • Interestingly, reaction of 7 with 3 equiv of NIS for 3 h gave a weak, transient EPR signal showing a nitrogen 1:1:1 triplet signal (g = 2.0053, a(N) = 1.55 mT at 9.414 GHz) consistent with a nitrogen centered radical/ radical cation (a) [Landoh-Bornstein, A.: Fischer, H., Hellwege, I.-H., Eds.; Springer-Verlag: Berlin, 1985; Vol. 9, Part d.
  • 31
    • 0000804936 scopus 로고    scopus 로고
    • (c) Shaffer, S. A.; Martin Sadílek, M.; Tureček, F. J. Org. Chem. 1996, 61, 5234] and might suggest alternative pathways. However, identical reaction outcomes were found in the absence of light, and attempts to trap putative radical intermediates, e.g., 2.5 equiv of methyl methacrylate, failed. Further mechanistic details are currently under investigation.
    • (1996) J. Org. Chem. , vol.61 , pp. 5234
    • Shaffer, S.A.1    Martin Sadílek, M.2    Tureček, F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.