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Volumn 8, Issue 7, 2006, Pages 1303-1306

Desulfonylation with Mg-MeOH-NiBr2: An expedient reagent system for the synthesis of 2-amino-2,3-dideoxy furanosides

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCOSIDE;

EID: 33645917681     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053082a     Document Type: Article
Times cited : (30)

References (26)
  • 8
    • 33645918660 scopus 로고    scopus 로고
    • note
    • The strategy has been implemented in the synthesis of D-lividosamine (2-amino-2,3-dideoxy-D-glucose), a constituent of aminoglycosides lividomycin-A, lividomycin-B, etc. Diastereoselective equatorial addition of ammonia to 1α (Figure 1) followed by the desulfonylation of the product at the C-3 site produced a known intermediate for accessing D-lividosamine. Several partially and fully protected analogues of D-lividosamine could be synthesized using N-monoalkylated and N-dialkylated amines in a similar approach. See ref 2b.
  • 10
    • 33645905818 scopus 로고    scopus 로고
    • note
    • All aminosugars 5a-c, 6a-c, and 7a-c described in Table 1 are single compounds. Structures of all compounds have been assigned on the basis of X-ray structural analysis and comparison of NMR data. These data will be reported elsewhere.
  • 11
    • 0033609760 scopus 로고    scopus 로고
    • For a review on desulfonylation, see: Najera, C.; Yus, M. Tetrahedron 1999, 40, 10547.
    • (1999) Tetrahedron , vol.40 , pp. 10547
    • Najera, C.1    Yus, M.2
  • 26
    • 33645930121 scopus 로고    scopus 로고
    • note
    • One of the reviewers suggested that the drop in yield was possibly due to the amines irreversibly binding to the greater quantities of Ni(0) reagent present.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.