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Volumn 352, Issue 16, 2010, Pages 2791-2798

Multicomponent synthesis of peptide-sugar conjugates incorporating hexafluorovaline

Author keywords

fluorine; glycoconjugates; multicomponent reactions; peptides

Indexed keywords


EID: 78349260875     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201000489     Document Type: Article
Times cited : (11)

References (53)
  • 1
    • 78349291476 scopus 로고    scopus 로고
    • For some reviews on MC reactions see
    • For some reviews on MC reactions see
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    • Two reviews
    • Two reviews
  • 21
  • 25
    • 57649243453 scopus 로고    scopus 로고
    • For a related process in which the Staudinger reaction has been exploited for the in situ preparation of carbodiimides in the MC sequential synthesis of hydantoins, see:
    • For a related process in which the Staudinger reaction has been exploited for the in situ preparation of carbodiimides in the MC sequential synthesis of hydantoins, see:, F. Olimpieri, A. Volonterio, M. Zanda, Synlett 2008, 3016 - 3020.
    • (2008) Synlett , pp. 3016-3020
    • Olimpieri, F.1    Volonterio, A.2    Zanda, M.3
  • 26
    • 0036430153 scopus 로고    scopus 로고
    • For a review see:, . See also
    • For a review see:, N. C. Yoder, K. Kumar, Chem. Soc. Rev. 2002, 31, 335 - 341. See also
    • (2002) Chem. Soc. Rev. , vol.31 , pp. 335-341
    • Yoder, N.C.1    Kumar, K.2
  • 29
    • 33746320232 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 4198 - 4203
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 4198-4203
  • 40
    • 78349258123 scopus 로고    scopus 로고
    • note
    • With an achiral carbodiimide the reaction is not stereoselective because the stereogenic α-amino acid ester steps in the process once the new stereogenic center is already formed (see the proposed mechanism). However, from the perspective of combinatorial application, the formation of both stereoisomers is not necessarily a drawback. The stereochemistry of the two diastereoisomers was assessed by X-ray diffraction of (S)- 6b (the reported stereochemistry is related to the new stereogenic center formed in the reaction, that is, the stereochemistry of hfVal) and on the basis of their spectroscopic and analytical features. The X-ray structure and relative full details will be published in a full paper.
  • 41
    • 78349276882 scopus 로고    scopus 로고
    • note
    • [9a]
  • 43
    • 78349249726 scopus 로고    scopus 로고
    • note
    • [9b]) and (ii) by treating 9 in acidic media, we observed the formation of hydantoin 14 probably through acid-catalyzed nucleophilic displacement of the alanine moiety by the tert-buyl-NH group.
  • 44
    • 78349231217 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the major diastereoisomer was assessed by X-ray diffraction of sugar-peptide conjugate (R)- 13f (see Supporting Information) and on the basis of their spectroscopic and analytical features. Full details will be given in a full paper.
  • 45
    • 78349233063 scopus 로고    scopus 로고
    • note
    • Also in this case, the diasteroisomeric glycosyl-hydantoin conjugates were recovered as by-products. A detailed study of the synthesis of such compounds will be published in a forthcoming paper.
  • 48
    • 24044489584 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 5329 - 5334
    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5329-5334


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.